Entertainment Music Best of the Chicago Blues Classic Windy City Blues from Muddy Waters, Howlin' Wolf and Others... Share PINTEREST Email Print Music Rhythm & Blues Top Picks Rock Music Pop Music Alternative Music Classical Music Country Music Folk Music Rap & Hip Hop World Music Punk Music Heavy Metal Jazz Latin Music Oldies Learn More By Reverend Keith A. Gordon Reverend Keith A. Gordon is known as the "Reverend of Rock 'n' Roll. He has 40+ years experience as a blues journalist, rock critic, and is the author of over 10 books about music. our editorial process Reverend Keith A. Gordon Updated March 08, 2017 The blues may have been born in the Mississippi Delta, but Chicago is the place that the music became a lasting part of American musical culture. With blues music pioneers like Big Bill Broonzy, Tampa Red, and Memphis Minnie blazing the trail for those who would follow, the Windy City became synonymous with not only a style of blues music but often times with the blues itself. A lot of great songs have come out of the city's long-vibrant blues scene; these are ten of the best Chicago blues songs. Big Bill Broonzy – "Key To The Highway" (1941) Big Bill Broonzy's Trouble In Mind. Photo courtesy Smithsonian Folkways Smart enough to recognize the changes on the horizon; Big Bill Broonzy was one of the few Delta bluesmen to make the successful leap towards the more urbanized Chicago blues sound of the 1930s and '40s. Broonzy's majestic "Key To The Highway," derived from the original piano blues song by Charlie Segar, was recorded in 1941 and has since become a blues standard. Although the best-known version of the song was recorded by Eric Clapton and his Derek and the Dominos band, Little Walter had an R&B chart hit with it in 1958, and it has been recorded by artists like Johnny Winter, Junior Wells, the Rolling Stones, and Freddie King. Buddy Guy – "First Time I Met The Blues" (1960) Buddy Guy's I Was Walking Through The Woods. Photo courtesy Geffen Records Buddy Guy's "First Time I Met The Blues" was more than just another great single release from the Chess Records blues factory, it was a musical statement announcing the guitarist's arrival as a creative force and a musician to be reckoned with on the competitive Chicago blues scene. Guy had recorded a couple of underperforming singles for Cobra Records before he signed with Chess, but the release of "First Time I Met The Blues," with its fiery guitar work and tortured, Robert Johnson-styled vocals, would kick off a significant half-decade of artistic triumphs for Guy and Chess. Howlin' Wolf – "The Red Rooster"(1961) Howlin' Wolf's Moanin' In The Midnight. Photo courtesy Geffen Records Picking just one Howlin' Wolf song as his "best" is a chore when you consider a catalog that holds classic songs like "Moanin' at Midnight," "Smokestack Lightnin'," "Evil," and "Wang Dang Doodle," among many others. Backed by the sublime leads of underrated guitarist Hubert Sumlin, Wolf's reading of Willie Dixon's "The Red Rooster" is a powerful, slow-burn blues with a healthy measure of slide guitar, potent drumming by Sam Lay, and Dixon's low-key upright bass. When it was covered by R&B great Sam Cooke a couple of years later as "Little Red Rooster," it would reach #11 on the Billboard pop chart; the Rolling Stones would score a #1 U.K. hit with the song in 1964. Jimmy Rogers – "Walking By Myself" (1956) Jimmy Rogers' Chicago Bound. Photo courtesy Price Grabber Guitarist Jimmy Rogers isn't nearly as well-known as he should be after spending years apprenticing at the side of the great Muddy Waters during the early-1950s. When Rogers left the Waters band in 1955 to pick up a solo career that he had begun in 1950, he recorded a couple of songs before hitting on "Walking By Myself." An adaptation of a T-Bone Walker song that Rogers had performed on, "Walking By Myself" is a smooth-as-silk fusion of rhythm and blues, with one of Rogers' most soulful vocal performances, Willie Dixon's strutting bassline, and Big Walter Horton's masterful harp accompaniment, which is, at turns, both sultry and spicy. Junior Wells – "You Don't Love Me, Baby" (1965) Junior Wells' Hoodoo Man Blues. Photo courtesy Delmark Records When Delmark Records' head Bob Koester recorded Junior Wells' classic album Hoodoo Man Blues, he was trying to capture the sound and feel of a sweaty blues romp at Theresa's Lounge, the South Side blues club where Wells and guitarist Buddy Guy ran the house band. Few songs articulate the Chicago blues sound better than "You Don't Love Me, Baby." With Guy on guitar (billed in the album's credits as "Friendly Chap"), delivering a nifty riff and trembling rhythms, Wells' belts out the lyrics in his typically understated style before cutting loose with a short harp solo near the song's end. Koko Taylor – "Wang Dang Doodle" (1965) Koko Taylor's Koko Taylor. Photo courtesy Geffen Records Songwriter Willie Dixon didn't like "Wang Dang Doodle," considering it the worst of the hits that he penned for Howlin' Wolf. As for the Wolf, he openly scorned the tune, considering it a "levee camp" song and beneath him, but he recorded it nonetheless and scored a hit. Dixon's dislike of the so-called "party song" didn't stop him from going to the well one more time when he produced Koko Taylor's version of it in 1965. With Taylor's robust pipes joyfully belting out the song's infectious chorus, it would rise to #4 on the Billboard R&B charts and reportedly sell more than a million copies. It has since been covered by everybody from rockers like Ted Nugent and Savoy Brown to the Pointer Sisters and 1990s alt-rock goddess P.J. Harvey. Little Walter – "Juke" (1952) Little Walter's His Best. Photo courtesy Geffen Records Little Walter Jacobs was Muddy Waters' harp player during the early-1950s when he recorded "Juke" at the tail-end of a Waters' session for Chess Records. A fluid, swinging instrumental with an easily-recognizable central riff and some tasty six-string fills courtesy of Jimmy Rogers, the song would spend an incredible 20 weeks on the Billboard magazine R&B charts, and hold the number one position in a chokehold for six of those weeks. With the song's success, Little Walter would skate away from the Waters band, steal away Junior Wells' backing band the Aces, and launch a solo career that remains one of the most significant in the Chicago blues. Magic Sam – "That's All I Need" (1967) Magic Sam's West Side Soul. Photo courtesy Delmark Records Although guitarist Magic Sam, the epitome of the West Side blues sound, recorded some better-known songs – his late-1950s Cobra Records hits like "All Your Love" and "Double Trouble" come to mind – it was his work on the classic 1967 album West Side Soul that cemented Sam's legacy. The album-opening "That's All I Need" is pure soul-blues magic, with impressive Sam Cooke-style vocals and infectious guitars, Sam layering his unique tone on top of Mighty Joe Young's simple but stunningly effective rhythm guitar. Muddy Waters – "Mannish Boy" (1955/1977) Muddy Waters' Hard Again. Photo courtesy Sony Legacy Recordings When rock 'n' roll pioneer Bo Diddley recorded "I'm A Man" in early 1955, he "borrowed" somewhat from Muddy Waters' 1951 blues hit "She's Moves Me," and released the song as the B-side to his hit "Bo Diddley." In response, Waters reworked the song as "Mannish Boy," an answer, of sorts, to Diddley's broadside, with a swaggering rhythm and easily-identifiable riff. Waters would record the song again some 20 years later with producer and guitarist Johnny Winter for his 1977 album Hard Again. "Mannish Boy" has been used in half-a-dozen films through the years and has subsequently been recorded by artists as diverse as Jimi Hendrix, Paul Butterfield, Elliott Murphy, and Hank Williams, Jr. Otis Rush – "I Can't Quit You Baby" (1956) Otis Rush's Classic Cobra Recordings. Photo courtesy Price Grabber Between 1956 and 1958, guitarist Otis Rush recorded a string of hits for Chicago's Cobra Records label, but it all started with "I Can't Quit You Baby." A slow, powerful twelve-bar blues song written and produced by the great Willie Dixon for Rush, the guitarist was spurred on by Dixon to deliver a passionate performance that has stood for the ages. The song hit #6 on the Billboard R&B chart that year, and would frequently be revisited by Rush throughout the years, recorded in differing versions as the circumstances required. Many other blues and blues-rock artists have also found the song alluring, as John Mayall's Bluesbreakers, Little Milton, Gary Moore, and Led Zeppelin have all recorded "I Can't Quit You Baby."