Entertainment Music The 10 Saddest Rap Songs Share PINTEREST Email Print Raymond Boyd/Getty Images Music Rap & Hip Hop Top Picks Basics Rock Music Pop Music Alternative Music Classical Music Country Music Folk Music Rhythm & Blues World Music Punk Music Heavy Metal Jazz Latin Music Oldies Learn More By Henry Adaso Henry Adaso Henry Adaso has written about hip-hop since 2005 and founded the award-winning blog The Rap Up. He has written for "Vibe," MTV, Rap Rehab, and more. Learn about our Editorial Process Updated on 07/13/18 Music wields a strong connection to emotions. There's no doubt that it can be therapeutic in stressful situations. Certain songs set our moods or activate specific memories as soon as we hear them. Whether you're bereaved or connected to someone who's currently mourning a loss, you'll find the following songs powerful and emotional. Here are the saddest rap songs ever. 01 of 10 Dr. Dre ft. Mary J Blige - "The Message" Ken Weingart/Michael Ochs Archives/Getty Images [Download] "I'm feeling like my whole world is blinded, Wondering why, crying, pouring out my heart."With a little help from Rell and Mary J Blige, Dre shed some gangsta tears for his deceased brother on this album closer from 2001. 02 of 10 Gangstarr - "Eulogy" Djamilla Rosa Cochran/WireImage [Download] "Eulogy" is a hip-hop funeral with Guru as the officiating clergy: "Mothers losing sons; Improper use of guns." Premo draws the procession to an end by running down a list of deceased notables and prays for the fallen soldiers to "rest in peace." Unfortunately, Guru would later join the long list of the dead. 03 of 10 Scarface - "I Seen a Man Die" Raymond Boyd/Michael Ochs Archives/Getty Images [Watch the Video] [Download] Scarface offers a riveting hip-hop ballad on "I Seen a Man Die." Assuming the role of a somber street prophet, 'Face delivers cautionary tales about the remorseless violence that has become commonplace in our society. 04 of 10 Puff Daddy ft. Faith Evans & 112 - "I'll Be Missin' You" SGranitz/WireImage/Getty Images [Download] Thanks to a Sauce Money-penned rhyme and a sample lifted from The Police's "Every Breath You Take," "I'll Be Missing You" captured the compelling sense of loss that eclipsed Biggie's murder in 1997. 05 of 10 Nas - "Dance" Scott Gries/ImageDirect/Getty Images [ Download ] On "Dance," Nas imagines one last tango with his mother Anne Jones, rhyming "Mom, you could never be replaced. I'd give it all up just to have one more dance." Jones lost her battle to cancer on April 7th, 2002. 06 of 10 2Pac - "Life Goes On" Raymond Boyd/Michael Ochs Archives/Getty Images A bottle of Hennessy in hand, Pac celebrates the life of his deceased loved ones before setting the scene for his own funeral: "Bury me smilin' with G's in my pocket/Have a party at my funeral Let every rapper rock it." 07 of 10 Bone Thugs-N-Harmony - "Tha Crossroads" Mitchell Gerber/Corbis/VCG via Getty Images [Download] Following Eazy-E's demise in March of 1995, his disciples Bone Thugs-N-Harmony unraveled this moody masterpiece in honor of the late N.W.A vet and other fallen soldiers. 08 of 10 The Notorious B.I.G. ft. 112 - "Miss U" Raymond Boyd/Michael Ochs Archives/Getty Images [Download] "Miss U" is one of the rare moments of warmth on Life After Death. Here, Biggie grieves the loss of a close friend and asks why he had to go. Ironically, Big himself would become the subject of several tributes and unanswered questions the same year. 09 of 10 T.I. ft. Jamie Foxx - "Live in the Sky" Jeff Kravitz/FilmMagic/Getty Images [Watch the Video] [Download] "Live in the Sky," one of the highlights of T.I.'s King LP, is a heartwrenching dedication to deceased friends and family. ( "My cousin Toot aint have to die right in front of his son and his wife He lost his life struggling over a gun.") About two months after King hit stores, T.I.'s personal assistant and childhood friend Philant Johnson was fatally gunned down. 10 of 10 Pete Rock & CL Smooth - "They Reminisce Over You" Catherine McGann/Getty Images [Watch the Video] [Download] "They Reminisce Over You" was inspired by the death of Troy Dixon (aka Trouble T-Roy), a close friend to Pete Rock & CL Smooth. It's a sentimental mélange of grief, uncertainty, and hope.