Entertainment Music

The Best 100 Songs From the 1990s

A girl lounging on a beanbag chair listening to music, surrounded by albums from the 1990s — LiveAbout / Hilary Allison

Pop Music
- 90s Hits
- Basics
- Reviews
- Top Picks
- Top Artists
- 80s Hits
Rock Music
Alternative Music
Classical Music
Country Music
Folk Music
Rap & Hip Hop
Rhythm & Blues
World Music
Punk Music
Heavy Metal
Jazz
Latin Music
Oldies

By

Updated on 09/07/19

From a pop musical standpoint, the 1990s was one of the most eclectic, and the best songs of the decade still sound fresh today. New acts like Nirvana changed the way people listened to rock music, while established stars like Madonna had the biggest hits of their careers. Boy bands and divas dominated the pop and dance charts, while East and West Coast rappers gave hip-hop a fresh sense of urgency.

So who were some of the biggest acts of the 1990s? Mariah Carey had more No. 1 hits than anyone else during that decade. Other artists who dominated the charts included Janet Jackson, Boyz II Men, Whitney Houston, and TLC. At the beginning of the '90s, Seattle birthed the grunge movement, which melded punk and hard rock, producing such influential bands as Pearl Jam and Soundgarden.

As the decade progressed, grunge was absorbed into the larger, radio-friendly "alternative rock" genre, then gave way to aggro-rock and nu-metal bands like Limp Bizkit and Linkin Park at the end of the decade. Fatboy Slim and the Chemical Brothers rejuvenated electronica, Shania Twain and Garth Brooks spurred a resurgence in the popularity of country music, and Jay-Z and Tupac Shakur brought new life to hip-hop.

Find out if your favorite song from the 1990s made the cut in this list of 100 hits from the decade.

01

of 100

Nirvana: 'Smells Like Teen Spirit' (1991)

Nirvana - Smells Like Teen Spirit — Nirvana - "Smells Like Teen Spirit". Courtesy DGC Records

The emergence of Nirvana's "Smells Like Teen Spirit" as a top-10 pop hit remains one of the most dramatic events in 1990s pop music. Kurt Cobain's sardonic ode to teenage angst, set to a pop melody pounded out by drums and guitars bathed in fuzzed-up distortion, rattled the pop music establishment. It was all accompanied by a music video that presented a memorable and unrelentingly dark view of the classic high school pep rally. Grunge had arrived.

02

of 100

Los Del Rio: 'Macarena' (1993)

Los Del Rio - Macarena — Los Del Rio - "Macarena". Courtesy RCA

Today, most people regard "Macarena" as having been ridiculously overplayed, a quirky relic for wedding reception dances only. The truth is that it was one of the most instantly entertaining and catchy hits of the decade.

Watch Video

03

of 100

Boyz II Men: 'End of the Road' (1992)

Boyz II Men - End of the Road — Boyz II Men - "End of the Road". Courtesy Motown

While their swiftly growing group of adoring fans waited for a second album, Boyz II Men recorded this ballad for the soundtrack to the Eddie Murphy film "Boomerang." The four-part crooning and gorgeous pleading fade are irresistible. Along with Whitney Houston's "I Will Always Love You," this became the second hit of 1992 to place on the all-time top-10 list of pop hits.

04

of 100

Elton John: 'Candle in the Wind 1997' (1997)

Elton John - Candle In the Wind 1997 — Elton John - "Candle In the Wind 1997". Courtesy A&M

The summer of 1997 came to a tragic close when Princess Diana died in a horrific car accident. The attention of the world was riveted on her funeral, and Elton John reworked his song "Candle in the Wind" for the occasion. It quickly became his biggest-selling single ever worldwide.

05

of 100

Tag Team: 'Whoomp! (There It Is)' (1993)

Tag Team - Whoomp! (There It Is) — Tag Team - "Whoomp! (There It Is)". Courtesy Life Records

Although no one is likely to assert that "Whoomp! (There It Is)" is art, it is possibly the most popular party single of the last 25 years. The incessant chant of "Whoomp! (There It Is)" could also be heard for many years as part of the soundtrack for breaks in sports events of all kinds. This is hip-hop at its most mindlessly fun.

06

of 100

Whitney Houston: 'I Will Always Love You' (1992)

Whitney Houston - I Will Always Love You — Whitney Houston - "I Will Always Love You". Courtesy Arista

The original version of "I Will Always Love You" was written and recorded by Dolly Parton. Whitney Houston's version was included on the soundtrack to the film "The Bodyguard," in which she starred along with Kevin Costner. With this song, one of music's most beautiful voices meets one of the most stunning ballads ever written, and it made history, becoming the biggest pop hit of all time.

07

of 100

Coolio: 'Gangsta's Paradise' (1995)

Coolio - Gangsta's Paradise — Coolio - "Gangsta's Paradise". Courtesy Tommy Boy

Prior to 1995, Coolio was mostly known for lighter, more humorous hip-hop, which provided an alternative to West Coast gangsta rap. Riveting and atmospheric, "Gangsta's Paradise" was such a shift in focus that Coolio's record label decided to leave it off his solo album and instead put it on the soundtrack to the film "Dangerous Minds." When released as a single, "Gangsta's Paradise" became one of the biggest hits of the year, spreading its social commentary on ghetto life from coast to coast.

08

of 100

Sinead O'Connor: 'Nothing Compares to You' (1990)

Sinead O'Connor - Nothing Compares 2 U — Sinead O'Connor - "Nothing Compares 2 U". Courtesy Chrysalis

It's difficult to remember now the image of Sinead O'Connor prior to the controversial television appearances that nearly brought down her career, but few pop performers have put together more powerful, heart-stopping performances than this. The song itself, written by Prince, is outstanding, but Sinead's emotional, gutsy performance made it a classic. Painful loss meets stunning vocal beauty with a perfectly understated instrumental arrangement.

09

of 100

R.E.M.: 'Losing My Religion' (1991)

R.E.M. - Losing My Religion — R.E.M. - Losing My Religion. Courtesy Warner Bros.

With the grunge revolution lurking just over the horizon, R.E.M., pioneers of alt-rock, burst into the mainstream with this song. Sparking dozens of conversations about its meaning, "Losing My Religion" is, in its most basic sense, a gorgeous folk-influenced pop tune about the feeling of going crazy.

10

of 100

Alanis Morissette: 'You Oughta Know' (1995)

Alanis Morissette - You Oughta Know — Alanis Morissette - "You Oughta Know". Courtesy Maverick

Alanis Morissette's debut sent shock waves through the music industry. No pop singer had ever laid bare the anger and pain of a relationship gone bad quite so explicitly. "You Oughta Know" clearly touched a nerve and led audiences into the complex, intricate songcraft of the phenomenally successful "Jagged Little Pill" album.

11

of 100

Jay-Z: 'Hard Knock Life (Ghetto Anthem)' (1998)

Jay-Z - Hard Knock Life — Jay-Z - Hard Knock Life. Courtesy Roc-a-Fella

Jay-Z consolidated his status as the best of the East Coast rappers with this brilliant single that transforms a show-stopping number from the Broadway musical "Annie" into a gripping hip-hop opus. It was proof of just how far hip-hop artists could push the boundaries of the genre.

Watch Video

12

of 100

Celine Dion: 'My Heart Will Go On (Love Theme From 'Titanic')' (1997)

Celine Dion - My Heart Will Go On — Courtesy Columbia

This song from the "Titanic" soundtrack was certainly one of the most overplayed ballads of the 1990s. Give it a fresh listen, though, and you'll realize just how beautiful the song is—and Celine Dion is no doubt one of the best voices in the business.

13

of 100

LL Cool J: 'Mama Said Knock You Out' (1990)

LL Cool J - Mama Said Knock You Out — Courtesy Def Jam

LL Cool J established himself as a top hard-edged rapper while still a teenager. By the end of the 1980s, though, he was being accused of selling out to pop audiences. "Mama Said Knock You Out" is his response to the criticism. It's a hard-hitting, aggressive rap classic that brought together both rap and pop audiences and cemented LL's status as one of the top rap artists of all time.

14

of 100

Backstreet Boys: 'I Want It That Way' (1999)

Backstreet Boys - I Want It That Way — Backstreet Boys - "I Want It That Way". Courtesy Jive Records

"I Want It That Way" is simply one of the great ballads in pop music history. It gave the Backstreet Boys the perfect opportunity to let their polished voices shine, and it became one of their biggest hits.

15

of 100

TLC: 'No Scrubs' (1999)

TLC - No Scrubs — TLC - "No Scrubs". Courtesy LaFace

The R&B trio TLC electrified the pop music world with their phenomenal album "Crazysexycool," released in 1994. Then it was a five-year wait for the next installment. Fortunately, "Fan Mail" was nearly as good as its predecessor. "No Scrubs," the leadoff single, is pitch-and-picture-perfect late '90s R&B.

16

of 100

Beck: 'Loser' (1994)

Beck - Loser — Beck - "Loser". Courtesy DGC

If any major pop hit from 1994 could be described as coming from left field, it would be Beck's "Loser." It's a bit like welding a killer self-deprecating chorus to Dylan's "Subterranean Homesick Blues." In the years to come, Beck would prove "Loser" was just a drop in the deep well of his creativity.

17

of 100

Fugees: 'Killing Me Softly' (1996)

Fugees - Killing Me Softly — Fugees - "Killing Me Softly". Courtesy Ruff House

On their second album, "The Score," the Fugees showed that hip-hop could be about much more than gangsters. Lauryn Hill's stunning voice was at the heart of this major-hit remake of Roberta Flack's "Killing Me Softly With His Song."

18

of 100

Ricky Martin: 'Livin' La Vida Loca' (1999)

Ricky Martin - Livin' La Vida Loca — Ricky Martin - "Livin' La Vida Loca". Courtesy Columbia

Ricky Martin began his career as a lead singer with the legendary boy band Menudo. By 1999, he was a household name with Latin music audiences. When "Livin' La Vida Loca" dropped, the English-speaking world discovered what they had been missing. It's irresistibly sexy and nearly impossible to listen to without moving the body.

19

of 100

Mariah Carey: 'Vision of Love' (1990)

Mariah Carey - Vision Of Love — Mariah Carey - "Vision Of Love". Courtesy Columbia

This No. 1 hit was the world's first introduction to the voice of Mariah Carey. Echoes of Whitney Houston's influence are evident, but the sheer power and swooping highs are all Mariah's own. This debut still ranks as one of her very best recordings.

20

of 100

Santana Featuring Rob Thomas: 'Smooth' (1999)

Santana featuring Rob Thomas - Smooth — Santana featuring Rob Thomas - "Smooth". Courtesy Arista Records

Who would have thought legendary Latin guitarist Carlos Santana would record one of the biggest pop hit singles of all time? Add to that, who would have thought its vocalist would be the lead singer for post-grunge band Matchbox 20? But it happened, and "Smooth" deserved its subsequent sales and acclaim. In 2005, Rob Thomas proved his performance on "Smooth" was no fluke by putting out the stellar solo album "...Something to Be."

21

of 100

John Mellencamp With Me'Shell NdegeOcello: 'Wild Night' (1994)

John Mellencamp with Me'Shell NdegeOcello - Wild Night — Courtesy Mercury

The pairing of Mellencamp and NdegeOcello on this irresistible pop song is a match made in rock and roll heaven. Together they took a Van Morrison chestnut and turned it into something transcendent. Turn this one up and try not to dance.

22

of 100

Lisa Loeb & Nine Stories: 'Do You Sleep?' (1995)

Lisa Loeb - Tails — Courtesy Geffen

Lisa Loeb rose quickly to stardom on the heels of her hit "Stay" from the soundtrack to the film "Reality Bites." "Do You Sleep?" is the first hit from her debut solo album, "Tails."

23

of 100

Billy Joel: 'River of Dreams' (1993)

Billy Joel River of Dreams — Courtesy Columbia

For the centerpiece of his 1993 album, Billy Joel put together this stream-of-consciousness, gospel-influenced recording. It spent three weeks at the top of the pop singles chart and is one of the most uplifting hits of Joel's career.

24

of 100

Sugar Ray: 'Every Morning' (1999)

Sugar Ray - Every Morning — Courtesy Atlantic

Sugar Ray's feel-good vibe is one of the pure pleasures of '90s pop music. This tale about a girlfriend who "has a halo hanging from the corner" of her four-poster bed is instantly recognizable and memorable.

25

of 100

Heart: 'All I Wanna Do Is Make Love to You' (1990)

Heart - All I Wanna Do Is Make Love To You — Courtesy Capitol Records

Although they are best known for a long string of rock hits going back to the 1970s, this ballad, written by Robert John "Mutt" Lange, was one of the group's biggest pop hits. The record's theme—a long night of lovemaking with a hitchhiker—was initially controversial, but at its core it's a fun fantasy straight out of a romance novel.

26

of 100

Blind Melon: 'No Rain' (1992)

Blind Melon - No Rain — Courtesy Capitol

The upbeat feel of Blind Melon's biggest hit, "No Rain," stands in contrast to the band's tragic history. Lead vocalist Shannon Hoon battled drug addiction through much of the early '90s and would be dead by late 1995 at the age of 28. Although many people remember the video for its sweet "dancing bee girl," the tune itself is much darker, outlining the efforts of bassist Brad Smith to cope with his girlfriend's struggles with clinical depression.

27

of 100

EMF: 'Unbelievable' (1991)

EMF - Unbelievable — Courtesy EMI

EMF rode the British invasion wave that broke on U.S. shores in the wake of the popularity of the Manchester dance scene. "Unbelievable" mixed intoxicating rhythms, sweet high vocals from lead singer James Atkin, and rousing shouts to storm to the top of the pop charts.

28

of 100

Whitney Houston: 'It's Not Right, But It's Okay' (1998)

Whitney Houston - It's Not Right But It's Okay — Courtesy Arista

By the time the '90s headed to a close, it had been eight years since Whitney Houston had put out a studio album. Music industry legend Clive Davis convinced her to record a new set of songs, and the resulting album, "My Love Is Your Love," includes some of her best work. "It's Not Right, But It's Okay" is a hard-hitting anthem for women on the way out of relationships that sounds great on the radio and on the dance floor.

29

of 100

Ben Folds Five: 'Brick' (1997)

Ben Folds Five - Brick — Courtesy Epic

Ben Folds and company brought the issue of abortion to the pop charts—from a male point of view. A particularly fascinating twist is that it seems the male narrator of this melancholy song is selfish and a bit of a jerk. Lyrically, this is one of the most unique hit songs of the '90s.

30

of 100

Arrested Development: 'Tennessee' (1992)

Arrested Development - Tennessee — Courtesy Chrysalis

Arrested Development finished their banner year by being awarded the Grammy for Best New Artist of 1992. The spiritual quest detailed in "Tennessee" was a big part of the band's success. The uplifting, intelligent lyrics and positive tone seemed to herald a new direction for rap, but it turns out that the gangsta takeover, just a year away, would win out.

31

of 100

Presidents of the United States of America: 'Lump' (1995)

Presidents of the United States of America - Lump — Courtesy Columbia

The humorous approach of Presidents of the United States of America stands out amid the onslaught of Seattle bands riding the wave of the grunge revolution. "Lump" straddles the line between punk and bubblegum pop, and the result is one of the most insanely catchy songs of the decade.

32

of 100

Barenaked Ladies: 'One Week' (1998)

Barenaked Ladies - One Week — Courtesy Reprise Records

For many, the mileage varied on the Barenaked Ladies' breakthrough hit. Its pure kinetic energy certainly invigorated pop radio playlists, debuting at No. 3 before eventually spending, appropriately enough, one week at No. 1. Although a little of its cheeky, self-indulgent humor can go a long way, few songs epitomize 90s pop like "One Week."

33

of 100

Marc Anthony: 'I Need to Know' (1999)

Marc Anthony - I Need To Know — Courtesy Columbia

The success of Ricky Martin early in 1999 opened the door for other Latin artists to enter the pop music mainstream. One of the most talented is Marc Anthony. "I Need to Know" was the perfect vehicle to land his gorgeous voice on the radio airwaves.

34

of 100

Shaggy: 'Boombastic' (1995)

Shaggy - Boombastic — Courtesy Virgin

Jamaican-born Orville Burrell had a huge hit with "Boombastic," one of the first dancehall—a sub-genre of reggae—songs to break through to the American pop charts. Shaggy, who took his stage name from a "Scooby Doo" character, exhibits oodles of personal charm alongside the funky grooves.

35

of 100

Oasis: 'Wonderwall' (1996)

Oasis - Wonderwall — Courtesy Creation Records

The brothers Gallagher—Liam and Noel—and their band, Oasis, helped usher in a new period of glory for British guitar pop, at least in the U.K. This is one of their few breakthrough American hits. It is gorgeous and irresistibly prods you into singing along.

36

of 100

Dishwalla: 'Counting Blue Cars' (1995)

Dishwalla - Counting Blue Cars — Courtesy A&M

We're still not sure exactly what this hit song is about, but it definitely is catchy. The ultimate hook in the lyric is the line "Tell me all your thoughts on God / Cause I'd really like to meet her," and it has something to do with asking questions, like children often do.

37

of 100

R.E.M.: 'Man on the Moon' (1992)

R.E.M. - Man on the Moon — Courtesy Warner Bros.

R.E.M.'s album "Automatic for the People" is one of the top artistic achievements of '90s pop music, and "Man on the Moon" is one of the most memorable and beautiful songs from that album. It is both a moving tribute to comedian Andy Kaufman and a thoughtful meditation on the power of popular culture.

Watch Video

38

of 100

Eric Clapton: 'Tears in Heaven' (1992)

Eric Clapton — Tim Mosenfelder/Getty Images

If you don't know its history, this song might seem a bit treacly, and it's certainly no match for a number of other Eric Clapton classics. But given that this gentle ballad was written in response to the death of Clapton's young son, Conor, it becomes one of the greatest songs of sorrow and comfort ever written. It was part of the soundtrack to the film "Rush," and Clapton's "Unplugged" album featured the even more popular acoustic rendition.

39

of 100

Alanis Morissette: 'Uninvited' (1998)

Alanis Morissette - Uninvited — Alanis Morissette - "Uninvited". Courtesy Maverick

This is one of Alanis Morissette's most memorable and lyrically uncluttered songs. The gothic, foreboding musical textures match well with her vocal intensity.

40

of 100

Spice Girls: 'Wannabe' (1996)

Spice Girls — Tim Roney/Getty Images

Even after the years of hype surrounding this all-girl group and its members, "Wannabe" is an exhilarating listening experience. "Girl power" from the group swept the U.K. in 1996 and then conquered America the following year.

41

of 100

Cranberries: 'Linger' (1993)

Cranberries - Linger — Cranberries - "Linger". Courtesy Island Records

Although later hits would more dramatically demonstrate the vocal acrobatics of the group's lead singer, Dolores O'Riordan, "Linger" has an almost ethereal beauty that does indeed remain long after the song ends. It was the chart debut of one of the most striking voices of the mid-1990s.

42

of 100

No Doubt: 'Don't Speak' (1995)

No Doubt - Don't Speak — No Doubt - "Don't Speak". Courtesy Interscope

This heartbreaking song about the end of a longtime love affair is somewhat of a stylistic anomaly given the rest of No Doubt's ska- and punk-influenced work. Still, it served to make the group's lead vocalist, Gwen Stefani, a bona fide star. The song's irresistible pop hooks kept it on the chart for most of the year.

43

of 100

Edwyn Collins: 'A Girl Like You' (1994)

Edwyn Collins - A Girl Like You — Edwyn Collins - "A Girl Like You". Courtesy Setanta

This Scottish performer put together one of the catchiest and most unique-sounding hits on '90s radio, sounding much like a more pop-oriented Iggy Pop. Unfortunately, Collins failed to replicate this success.

Watch Video

44

of 100

Marky Mark and the Funky Bunch: 'Good Vibrations' (1996)

Marky Mark and the Funky Bunch - Good Vibrations — Marky Mark and the Funky Bunch - Good Vibrations. Courtesy Interscope

"Good Vibrations" introduced the world to Mark Wahlberg (aka Marky Mark), the younger brother of Donnie Wahlberg, a member of New Kids on the Block. Mark Wahlberg had a history of scrapes with the law as a teenager, but his ready-for-video buffed body and good looks, combined with energetic dance beats and Loleatta Holloway's diva-esque vocals, made for a smash pop hit. Mark Wahlberg never repeated this musical success, but he has moved on to be a well-respected movie actor.

45

of 100

R. Kelly: 'Bump 'n Grind' (1993)

R. Kelly - Bump n' Grind — R. Kelly - "Bump n' Grind". Courtesy Jive Records

This song demonstrates exactly why we fell in love with the music of R. Kelly, if not the man. The a cappella anguish in Kelly's voice in the song's opening is brilliant, and it becomes an amazingly sexy song. "Bump 'N Grind" connects the vocal stylings of early '90s new jack swing with the romance of classic R&B.

46

of 100

Us3: 'Cantaloop (Flip Fantasia)' (1993)

Us3 - Cantaloop (Flip Fantasia) — Us3 - "Cantaloop (Flip Fantasia)". Courtesy Blue Note

Us3 created a unique sound by placing contemporary rap rhymes on top of samples of classic jazz from the Blue Note record label. "Cantaloop (Flip Fantasia)" is built on a Herbie Hancock sample from "Cantaloupe Island." The fusion didn't always work well, but this time it did, and the overall effect is eminently engaging.

47

of 100

Jesus Jones: 'Right Here Right Now' (1991)

Jesus Jones - Doubt — Jesus Jones - Doubt. Courtesy SBK

The band Jesus Jones rode the same wave from the U.K. to American shores that carried EMF. "Right Here Right Now" is less frenetic than EMF's "Unbelievable," but it settled easily into the pop mainstream and quickly rose to the top of the pop singles chart.

48

of 100

Will Smith: 'Gettin' Jiggy Wit It' (1997)

Will Smith - Gettin' Jiggy Wit It — Will Smith - "Gettin' Jiggy Wit It". Courtesy Sony

Will Smith's first solo effort resulted in this catchy and cool single. His brand of clean, good-humored, party hip-hop caught on instantly. Like Mark Wahlberg, he went on to enjoy way more success as an actor, but this remains one of the more charming pop musical relics of the 1990s.

49

of 100

Madonna: 'Secret' (1994)

Madonna - Secret — Madonna - "Secret". Courtesy Warner Bros.

"Secret" is one of the least flamboyant of Madonna's 1990s hits, but it remains one of her most satisfying. It features a mid-tempo beat and some of the most warm and inviting vocals the singer has ever recorded.

50

of 100

Quad City DJs: 'C'mon 'n Ride It (The Train)' (1996)

Quad City DJs - C'mon Ride It (The Train) — Quad City DJs - "C'mon Ride It (The Train)". Courtesy Quadrasound

The producers behind the irresistibly catchy "Whoomp! (There It Is)" came up with another irresistible party hit. "C'mon 'N Ride It (The Train)" inspired another wave of soundalike hits and is perennially welcome on any party soundtrack.

Watch Video

51

of 100

Bell Biv Devoe: 'Poison' (1990)

Bell Biv Devoe - Poison — Bell Biv Devoe - "Poison". Courtesy MCA

In the wake of the disintegration of New Edition, three of the group's members, Ricky Bell, Michael Bivins, and Ronnie DeVoe, proved that Bobby Brown wasn't the only breakout talent in the group. The hard-edged funky R&B of "Poison" spearheaded the development of new jack swing as one of the freshest sounds in R&B in a decade.

52

of 100

Faith No More: 'Epic' (1990)

Faith No More - Epic — Faith No More - "Epic". Courtesy Reprise Records

This top-10 hit from San Francisco's Faith No More was both heavy and absurd. A set of inscrutable lyrics meets a punk/funk/rap beat and the result is one of the most exhilarating aural experiences of any decade.

53

of 100

Martin Page: 'In the House of Stone and Light' (1994)

Martin Page - In the House of Stone and Light — Martin Page - In the House of Stone and Light. Courtesy Mercury

This effortless mainstream pop nugget followed Page's success as songwriter of such hits as Starship's "We Built This City" and Heart's "These Dreams." "In the House of Stone and Light" is not artistically innovative, but it nearly perfectly encapsulates the mainstream of pop circa 1995. Page faded from the airwaves not long after this one hit.

54

of 100

Tracy Chapman: 'Give Me One Reason' (1995)

Tracy Chapman - New Beginning — Tracy Chapman - New Beginning. Courtesy Elektra

Most pop fans thought Tracy Chapman would be relegated to the annals of one-hit-wonderdom based on the success of "Fast Car" from her first album. Then she reappeared with this deeply bluesy crowd pleaser, proving that there is still room for innovation and surprise within the genre.

55

of 100

House of Pain: 'Jump Around' (1992)

House of Pain - Jump Around — House of Pain - "Jump Around". Courtesy XL Recordings

For a brief period of time in the 1990s (see Faith No More), it seemed that the marriage of edgy rock and hip-hop could actually become a thing. "Jump Around" is proof that the union could either be incredibly infectious or annoying, depending on one's tolerance for the incessant siren that accompanies the pounding beats. Unfortunately, House of Pain never did recapture this moment of greatness.

56

of 100

Digital Underground: 'The Humpty Dance' (1990)

Digital Underground - Sex Packets — Digital Underground - Sex Packets. Courtesy Tommy Boy

Some might dismiss this song as simply a novelty hit, but it deserves closer listening. As hip-hop was moving further into the mainstream, this group from Oakland distinguished itself by backing goofy raps with hot Parliament-Funkadelic-inspired funk. Rarely has a pop classic made sex sound so fun and funny.

57

of 100

Michael Jackson: 'Black or White' (1991)

Michael Jackson - "Black Or White" — Michael Jackson - "Black Or White". Courtesy Epic Records

This is arguably the last great Michael Jackson single. It features Guns 'n Roses guitarist Slash ushering in an uplifting message about racial unity. As was the norm for Michael Jackson releases at the time, the song was accompanied by a big-budget video. This one was directed by John Landis and featured actors Macaulay Culkin, George Wendt, and Peggy Lipton.

58

of 100

DJ Jazzy Jeff and the Fresh Prince: 'Summertime' (1991)

DJ Jazzy Jeff and the Fresh Prince - Summertime — DJ Jazzy Jeff and the Fresh Prince - "Summertime". Courtesy Jive Records

D.J. Jazzy Jeff and Will Smith (aka the Fresh Prince) took a big step forward in the maturity of their sound with the 1991 album "Homebase." "Summertime," their biggest hit, is the centerpiece of the album. Its laid-back grooves settled in as the summer song of 1991.

59

of 100

Sarah McLachlan: 'Adia' (1997)

Sarah McLachlan - Adia — Sarah McLachlan - "Adia". Courtesy Arista

Sarah McLachlan's voice is almost otherworldly in its beauty. This single came out as the all-female Lilith Fair concert tour, organized by McLachlan, was just kicking into gear. It remains one of the anthems of that particular period, when women in rock were asserting themselves on the airwaves and on the stage.

60

of 100

Janet Jackson: 'Escapade' (1990)

Janet Jackson - Escapade — Janet Jackson - "Escapade". Courtesy A&M Records

Taken from Janet Jackson's hit-filled concept album "Rhythm Nation: 1814," "Escapade" at first seems like a simple, light piece of pop fluff. After listening to it multiple times, however, its escapist charm sinks in. This was one of the most joy-filled hits of 1990, an atmosphere further enhanced by the accompanying video.

61

of 100

Wreckz N Effect: 'Rump Shaker' (1992)

Wreckz-N-Effect - Rump Shaker — Wreckz -N-Effect - "Rump Shaker". Courtesy MCA

"All I wanna do...zooma zoom zoom zoom..." At this point, hip-hop began to walk the fine line between pop radio acceptability and unacceptably explicit sexual content. "Rump Shaker" is innocent by today's standards, but it pushed boundaries in its day.

62

of 100

Collective Soul: 'The World I Know' (1995)

Collective Soul - The World I Know — Collective Soul - "The World I Know". Courtesy Atlantic

"So I walk up on high / And I step to the edge / To see my world below." Rock band Collective Soul pulled out all of the stops musically, including soaring strings, to support this beautiful ballad. An outstanding music video added more resonance to this powerful song.

63

of 100

Melissa Etheridge: 'Come to My Window' (1993)

Melissa Etheridge - Come To My Window — Melissa Etheridge - "Come To My Window". Courtesy Island

Although her style is often thought of as overly earnest, Etheridge can also be gut-wrenching. "Come to My Window" conjures up a powerful picture of romantic angst and erotic tension, accompanied by the artist's straightforward guitar-playing and raspy vocals.

64

of 100

Wallflowers: 'One Headlight' (1996)

Wallflowers - Bringing Down the Horse — Wallflowers - Bringing Down the Horse. Courtesy Interscope

This band, led by Bob Dylan's son Jakob, spent over a year on the pop singles chart with this quiet masterpiece. Jakob Dylan's vocals have an alluring world-weariness that at times are a dead ringer for Tom Petty's voice.

65

of 100

Stereo MCs: 'Connected' (1992)

Stereo MC's - Connected — Stereo MC's - "Connected". Courtesy Island

Stereo MCs became one of the most successful of the British hip-hop acts. "Connected" is propelled by a catchy but downbeat atmospheric brand of hip-hop.

66

of 100

Amy Grant: 'Baby Baby' (1991)

Amy Grant - Baby Baby — Amy Grant - Baby Baby. Courtesy A&M

Amy Grant spent the 1980s as one of the most successful of the Christian pop singers, but not until 1991 did she enjoy a major crossover into the pop mainstream. "Baby Baby" is a delightful celebration of love between life partners.

67

of 100

Various Artists: 'ESPN Presents the Jock Jam' (1997)

Various Artists - ESPN Presents Jock Jams Vol. 1 — Various Artists - ESPN Presents Jock Jams Vol. 1. Courtesy Tommy Boy

This medley will win no prizes for art, but it welds together some of the most popular songs used at sporting events and was nearly inescapable in 1997. Kicking off with the immortal "Are you ready to rumble..." this pop culture artifact is sure to get your blood pumping with snippets from such tracks as "Whoomp! There It Is," "It Takes Two," "YMCA," and "Pump Up the Jam."

68

of 100

TLC: 'Waterfalls' (1994)

TLC - Waterfalls — TLC - "Waterfalls". Courtesy LaFace

Slinky, gently insistent backing horns and guitar combine with smooth, languid vocals to create an instant R&B classic. Beyond its audio appeal, "Waterfalls" is a disturbing commentary on street violence and its impact on the lives of young Black men.

69

of 100

Seal: 'Kiss From a Rose' (1991)

Seal - Kiss From a Rose — Seal - "Kiss From a Rose". Courtesy Warner Bros.

This was another single saved from obscurity by its inclusion on a movie soundtrack. "A Kiss From a Rose" was featured as the love theme in the film "Batman Forever." Seal's perfectly balanced, acrobatic, romantic vocals make this otherwise simply pleasant song a work of art.

70

of 100

Deborah Cox: 'Nobody's Supposed to Be Here' (1998)

Deborah Cox - Nobody's Supposed To Be Here — Deborah Cox - "Nobody's Supposed To Be Here". Courtesy Arista

This song, a gorgeous R&B ballad revved up with a club mix, was one of the top dance hits of the decade. Record industry execs intended Deborah Cox to be the next Whitney Houston. That didn't quite work, but she did contribute this timeless smash.

71

of 100

Counting Crows: 'Mr. Jones' (1993)

Counting Crows - Mr. Jones — Counting Crows - "Mr. Jones". Courtesy Geffen

The voice of Counting Crows' lead vocalist, Adam Duritz, is a magnificent instrument. "Mr. Jones" introduced music fans to the singer's amazing ability to tell a story within the context of a song. Try to sing along, and after you finish gasping for breath, you'll realize just how phenomenal this performance is.

72

of 100

Dr. Dre: 'Nuthin' But a 'G' Thang' (1992)

Dr. Dre - Nothin' But a G Thang — Dr. Dre - "Nothin' But a G Thang". Courtesy Death Row

This single and the album it came from, Dr. Dre's "Chronic," took hip-hop down an entirely new road, one that would eventually be known as gangsta rap. "Nuthin' But a 'G' Thang" features Dre's protege Snoop Doggy Dogg, who would soon become a star on his own. Fat, Parliament-style funky beats, laidback rap vocals, words reflecting the violence of life on the street, and pop hooks combined for a tremendously successful new sound.

Watch Video

73

of 100

Backstreet Boys: 'Everybody (Backstreet's Back)' (1997)

Backstreet Boys - Everybody (Backstreet's Back) — Backstreet Boys - "Everybody (Backstreet's Back)". Courtesy Jive Records

With the current backlash against boy bands, too few remember that these male vocal groups have recorded some great pop songs. This is the masterpiece that helped the Backstreet Boys conquer the hearts of millions.

74

of 100

C&C Music Factory: 'Gonna Make You Sweat' (1990)

C and C Music Factory - Gonna Make You Sweat — C and C Music Factory - Gonna Make You Sweat. Courtesy Columbia

Inspired by the powerful beats of house music, hit after hit crossed over from the dance chart to the pop top-10 in 1990—but it took producers Robert Clivilles and David Cole (aka C&C Music Factory) to climb all the way to No. 1. "Gonna Make You Sweat" featured the powerful vocals of Martha Wash and a rap from Freedom Williams along with state-of-the-art house rhythms to make up one of the most exhilarating songs of the year.

75

of 100

Bruce Springsteen: 'Streets of Philadelphia' (1993)

Bruce Springsteen - Streets Of Philadelphia — Bruce Springsteen - "Streets Of Philadelphia". Courtesy Columbia

Jonathan Demme's "Philadelphia" was the first big-budget, mainstream motion picture to deal directly with the AIDS epidemic, and "Streets of Philadelphia" is the perfect theme for it. With it, Springsteen creates an atmosphere of darkness and loneliness that still manages to maintain a sense of dignity. The song won a much-deserved Academy Award for Best Song from a Motion Picture.

76

of 100

Dave Matthews Band: 'Crash Into Me' (1996)

Dave Matthews Band - Crash Into Me — Dave Matthews Band - "Crash Into Me". Courtesy RCA

Although the lyrics invite ambiguous interpretation, for many this is one of the most unabashedly erotic songs of the decade. Listen and enjoy Matthews' intimate vocals over intricately arranged bluegrass-tinged pop.

77

of 100

MC Hammer: 'U Can't Touch This' (1990)

MC Hammer - U Can't Touch This — MC Hammer - "U Can't Touch This". Courtesy Warner Bros.

The importance of MC Hammer to pop music history was his ability to prove without a doubt that rap could be as effortlessly entertaining as any other musical genre. "U Can't Touch This" is little more than Hammer's simple rap superimposed over Rick James' "Super Freak," but the image of Hammer working the crowd in his oversized parachute pants is one of the most memorable pop cultural moments of 1990.

78

of 100

Ini Kamoze: 'Here Comes the Hotstepper' (1994)

Ini Kamoze - Here Comes the Hotstepper — Ini Kamoze - "Here Comes the Hotstepper". Courtesy Columbia

Selected to play a key role on the soundtrack for Robert Altman's exploration of the fashion world in the movie "Pret-a-Porter," "Here Comes the Hotstepper" brought dancehall into the mainstream, and introduced the world to Jamaican slang for a man on the run from the law. It remains one of the catchiest songs of the mid-'90s.

79

of 100

Lauryn Hill: 'Doo Wop (That Thing)' (1998)

Lauryn Hill - Doo Wop (That Thing) — Lauryn Hill - "Doo Wop (That Thing)". Courtesy Columbia

After the far too early breakup of the Fugees, the music world waited impatiently for Lauryn Hill's first solo effort. The wait was worth it. "The Miseducation of Lauryn Hill" is one of the top albums of the decade, and "Doo Wop (That Thing)" is a brilliantly tuneful dissection of sexual politics from the point of view of both genders.

80

of 100

Puff Daddy and Faith Evans Featuring 112: 'I'll Be Missing You' (1997)

Puff Daddy and Faith Evans feat. 112 - I'll Be Missing You — Puff Daddy and Faith Evans feat. 112 - "I'll Be Missing You". Courtesy Bad Boy Entertainment

Rap star Notorious B.I.G. (Biggie Smalls) was tragically gunned down in March 1997. His recording partner, Puff Daddy—now known alternately as Sean Combs, P Diddy, or just Diddy—put together this moving memorial with Smalls' widow, Faith Evans, and the vocal group 112. It memorably samples the Police classic "Every Breath You Take" and became a favored memorial track of the late '90s.

Watch Video

81

of 100

Gloria Estefan: 'Coming out of the Dark' (1991)

Gloria Estefan - Coming Out of the Dark — Gloria Estefan - Coming Out of the Dark. Courtesy Epic

In March 1990, Gloria Estefan, her husband, and her son were all injured when a truck struck their tour bus. Gloria suffered a fractured vertebra and was unable to tour for a year. The accident and long recovery inspired this gorgeous hit ballad. "Coming out of the Dark" is now considered one of the top inspirational pop hits of all time.

82

of 100

Shawn Colvin: 'Sunny Came Home' (1996)

Shawn Colvin - A Few Small Repairs — Shawn Colvin - A Few Small Repairs. Courtesy Columbia

Sunny, the protagonist of this folkie song, comes home with some matters to settle. Parts of this song can send chills up your spine, while Colvin's voice gently lulls you back into the story.

83

of 100

Smashing Pumpkins: '1979' (1995)

Smashing Pumpkins - 1979 — Smashing Pumpkins - "1979". Courtesy Virgin

Within the context of "Melon Collie and the Infinite Sadness," an expansive double album dedicated to depression, "1979" sounds almost perky. It's gentle sense of nostalgic reverie most definitely jibed with the decade's mood of inward contemplation.

84

of 100

Red Hot Chili Peppers: 'Under the Bridge' (1991)

Red Hot Chili Peppers - Under the Bridge — Red Hot Chili Peppers - "Under the Bridge". Courtesy Warner Bros.

It's ironic that a gentle ballad became the breakthrough hit for a band best known for blending classic uptempo funk with alternative rock. The song emerged out of lead vocalist Anthony Kiedis' struggles to overcome heroin addiction. After the addiction destroyed a number of his personal relationships, Kiedis reflected on his relationship with the city of Los Angeles itself. "Under the Bridge" made it all the way to No. 2 on the pop singles chart.

85

of 100

Hanson: 'MMMBop' (1997)

Hanson - MmmBop — Hanson - "MmmBop". Courtesy Mercury Records

The Hanson brothers brought back bubblegum pop in all of its glory. "MMMBop" is catchy, sugary sweet, and irresistible. Just try to avoid singing along.

86

of 100

Blackstreet: 'No Diggity' (1996)

Blackstreet - No Diggity — Blackstreet - "No Diggity". Courtesy Interscope

This is the peak of the work created by producer, songwriter, and performer Teddy Riley, leader of the group Blackstreet. He is one of the top R&B masters of the 1990s and a key architect of new jack swing. "No Diggity" is that genre fully refined.

87

of 100

U2: 'Mysterious Ways' (1991)

U2 - Mysterious Ways — U2 - "Mysterious Ways". Courtesy Island

After their dramatic success with "The Joshua Tree" and an epic concert tour of the U.S., U2 completely reinvented their musical style on the album "Achtung Baby." Glorious pretensions gave way to some of the sexiest funky rock of the decade. "Mysterious Ways" features sinuous guitar work from The Edge and gospel-influenced vocals from Bono that drive home one of U2's most uninhibited pop-rock songs.

88

of 100

Soul Asylum: 'Runaway Train' (1992)

Soul Asylum - Runaway Train — Soul Asylum - "Runaway Train". Courtesy Columbia

Soul Asylum shot to the top of the ranks of alt-rock bands with this folkish classic. The video for "Runaway Train" was accompanied by advertisements about missing children, serving a powerful public service. Many alt-rock fans abandoned Soul Asylum as having sold out to the mainstream, but pop fans pushed "Runaway Train" to No. 5 on the charts, and it became a well-deserved classic.

89

of 100

Deee-Lite: 'Groove Is in the Heart' (1990)

Deee-Lite - Groove Is In the Heart — Deee-Lite - "Groove Is In the Heart". Courtesy Elektra

In a dance-happy pop environment, this trio swept in with a classic that still sounds half-retro, half-contemporary, and completely groovy. "Groove Is in the Heart" effortlessly glides across genres from hip-hop to house and funk. Guest musicians—including Bootsy Collins, Fred Wesley, Maceo Parker, and A Tribe Called Quest's Q-Tip—boost the party atmosphere. This was the song of summer 1990.

90

of 100

4 Non Blondes: 'What's Up?' (1992)

4 Non Blondes - What's Up — 4 Non Blondes - "What's Up". Courtesy Interscope

"What's Up?" seemingly appeared out of nowhere, becoming a neo-folkie hit first on modern rock radio stations and then on the pop charts. Although it only reached No. 11, it has been a radio fixture ever since. The group never duplicated the success of this song, but lead vocalist Linda Perry went on to become a successful songwriter and producer, crafting hits for everyone from Pink to Courtney Love.

91

of 100

Madonna: 'Vogue' (1990)

Madonna - Vogue — Madonna - "Vogue". Courtesy Warner Bros.

It was not really part of any album project but rather was added to the soundtrack album of "Dick Tracy." "Vogue" was also significantly late in spotlighting the underground world of "voguing," but it is possibly the most perfect dance song Madonna has ever recorded. The acclaimed David Fincher video wraps up a stunning pop-dance package.

92

of 100

Mariah Carey: 'Fantasy' (1995)

Mariah Carey - Fantasy — Mariah Carey - "Fantasy". Courtesy Columbia

Using Tom Tom Club's instrumental track from "Genius of Love" as a backdrop to Mariah Carey's effortlessly soaring vocals was a stroke of genius. This romantic gem remains the best single recording of Carey's phenomenal career.

93

of 100

Cher: 'Believe' (1998)

Cher - Believe — Cher - "Believe". Courtesy Warner Bros.

No one really doubted Cher would eventually make another musical comeback, but this time it became the biggest hit of her entire career. "Believe" is a perfect piece of dance-pop, and it took the entire world by storm. More dance hits followed in its wake, along with a farewell concert tour that lasted more than three years. Cher is certainly someone who believes in "life after love."

94

of 100

Proclaimers: 'I'm Gonna Be (500 Miles)' (1988/1993)

Proclaimers - I"m Gonna Be (500 Miles) — Proclaimers - "I'm Gonna Be (500 Miles)". Courtesy Chrysalis

"I'm Gonna Be (500 Miles)" was originally released in 1988, but upon its inclusion in the "Benny and Joon" movie soundtrack, the energetic pop-rock tune became a '90s hit and is now a classic. The Proclaimers are comprised of the Scottish duo of Craig and Charlie Reid, who created an energetic, infectious brand of pop-rock with influences from their Scottish background.

95

of 100

Boyz II Men: 'Motownphilly' (1991)

Boyz II Men - Motownphilly — Boyz II Men - "Motownphilly". Courtesy Motown

This remains one of the best-ever autobiographical songs by a pop recording artist. "Motownphilly" details the group's discovery by Michael Bivins, of New Edition and Bell Biv Devoe fame, and their first taste of stardom. The a cappella break is simply gorgeous.

96

of 100

Sheryl Crow: 'All I Wanna Do' (1999)

Sheryl Crow - All I Wanna Do — Sheryl Crow - "All I Wanna Do". Courtesy A&M

With the words "This ain't no disco. It ain't no country club either. This is L.A.," the world was introduced to the neo-folkie, irresistible pop of Sheryl Crow. "All I Wanna Do" unfolds like a mini-movie thanks to Crow's artful vocals, whose lyrics paint a luminous picture of the adventures of Sheryl and "Billy" "until the sun comes up over Santa Monica Boulevard."

Watch Video

97

of 100

Madonna: 'Ray of Light' (1998)

Madonna - Ray Of Light — Madonna - Ray Of Light. Courtesy Warner Bros.

Madonna explored the pop potential of electronica with her first completely new studio album in four years. Working with collaborator William Orbit, the result is fresh, new, and invigorating. "Ray of Light" is aptly named, for it's a luminous, extremely danceable, and artful piece of techno.

98

of 100

Smash Mouth: 'Walkin' on the Sun' (1997)

Smash Mouth - Fush Yu Mang — Smash Mouth - Fush Yu Mang. Courtesy Interscope

The ska-punk-bound Smash Mouth burst into the spotlight with this catchy slab of '60s psychedelic soul. Unfortunately, the band never quite returned to the glory of this single, but it is one of the greatest tracks of the decade.

99

of 100

Everything But the Girl: 'Missing' (1994)

Everything But the Girl - Missing — Everything But the Girl - "Missing". Courtesy Atlantic

"Like the deserts miss the rain..." Remixed in countless ways over the years, there has never been a more powerful expression of emotional and sexual longing in pop music than that at the core of "Missing." In a year marked by wistfulness and longing in pop songs, this is the peak.

100

of 100

Britney Spears: '...Baby One More Time' (1998)

Britney Spears ... baby one more time. Courtesy Jive Records

She first gained national notice as a member of "The New Mickey Mouse Club" on Disney's cable network, but it was as a pop singer that Britney Spears became the most watched celebrity in the world. Her first single "...Baby One More Time" is a brilliant piece of pop music. It's catchy and sexy, and it sports a mildly controversial video that still has people talking today.