The Realest S*** I Ever Wrote: 20 of Your Favorite Rappers' Realest Songs

These songs capture rappers at their most vulnerable and perceptive moments.

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Complex Original

Image via Complex Original

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“Real” is a loaded word in hip-hop, carrying connotations of honesty and authenticity that go beyond a rapper simply proving his or her street cred or dropping a few autobiographical details into lyrics. And all major stars in hip-hop seems to have their own ideas of how to define it. 2Pac's description of his work as “real” might be the same vision that Drake has when he uses the word today. But real heads know real when they hear it, and there are certain songs have become treasured as the moments when lyricist were especially vulnerable and revealing about their own lives, or just more perceptive about the world we all live in. These are 20 of Your Favorite Rappers' Realest Songs.

Written by Al Shipley (@alshipley​), Insanul Ahmed (@Incilin), & Angel Diaz (@ADiaz456)

The Notorious B.I.G. “Suicidal Thoughts” (1994)

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Producer: Lord Finesse

Album: Ready to Die

It’s sometimes glossed over, amidst the Bad Boy legacy of shiny suits and pop samples, just how dark the Notorious B.I.G.’s music could be. And if the title of his landmark debut didn’t make it obvious enough, the album’s closing track underlined the dark self-destructive streak that ran through Christopher Wallace’s music well before his violent, untimely end. “I know my mother wished she got a fucking abortion,” he deadpans, as Puff Daddy pleads on the other end of the phone line not take the conversation where he knows it’s going. The entire phone call conceit is a little stagey (and at times recalls the format of DJ Jazzy Jeff & The Fresh Prince’s “Nightmare on My Street”) but every word of Big’s self-loathing monolog feels a little too real to be just another edgy concept song to close a gangsta rap album. —Al Shipley

Scarface “I Seen a Man Die” (1994)

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Producer: Mike Dean, Scarface, N.O. Joe

Album: The Diary

Scarface’s unlikely first top 40 solo hit was atypical for the pop charts, but the track’s somber meditation on mortality wasn’t out of the ordinary for the Geto Boys leader’s groundbreaking songwriting. The song contains moments of hope, in the first verse’s tale of a man getting out of jail and vowing to turn his life around. But much of it deals with the physical realities of a body dying, or the fate of a soul after committing murder, each verse concluding with Face’s chilling realization that “I could never see a man cry, 'til I seen a man die.” —Al Shipley

2Pac “Dear Mama” (1995)

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Producer: Tony Pizarro, DF Master Tee, Moses

Album: Me Against the World

In hip-hop, most songs about fathers are ambivalent pieces about absent or imperfect dads, while the songs about mothers are mostly affectionate odes to devoted moms. But the most famous mama song in the rap canon is one of its most complex. The lead single to Me Against the World, the album that helped raise 2Pac to the status of a cultural icon, touches on his mother Afeni Shakur’s activism and incarceration as a member of the Black Panther Party before her son’s birth. But 2Pac doesn’t shy away from the times when Afeni wasn’t there for her son, when her drug addiction and her commitment to activism took precedent over motherhood.

Ultimately, however, the song radiates with the warmth of the rapper’s eventual reconciliation with his mother, and his acknowledgment of the kind of flawed, passionate humanity they had in common. Pac would later call his song “Against All Odds” the “realest shit I ever wrote” (giving this post its title), and even though that’s an amazing song, “Dear Mama” carries a different emotional punch. —Al Shipley

Ghostface Killah “All That I Got Is You” (1996)

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Producer: RZA

Album: Ironman

Ghostface’s emphatic delivery on some tracks has often sounded like he’s on the verge of tears, but he’s never revealed so much that it really seems like he might be crying as on “All That I Got Is You.” A year after Mary J. Blige helped make Method Man a pop star with a romantic duet, she blessed another Wu-Tang member’s solo single, this time putting her soul into a hook while Ghost filled the verses with remembrances of his childhood. And in typical Ghostface fashion, he took a fairly commonplace rap song premise, of having grown up in poverty, and brought it to life with well-observed, slice-of-life details and word choices, “And there was days I had to go to Tex house with a note/Stating, 'Gloria can I borrow some food? I'm dead broke.'” —Al Shipley

Jay Z “You Must Love Me” (1997)

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Producer: Nashiem Myrick for The Hitmen

Album: In My Lifetime, Vol. 1

“You Must Love Me” is the hardened heart at the center of Jay Z’s most under-appreciated album, In My Lifetime, Vol. 1. Although many of his early albums feature tales of the dope game, and some are more overtly drawn from the mythology of his own youthful misadventures, “You Must Love Me” spins a series of more writerly yarns about family, betrayal, forgiveness, and regret. Jay rhymes about selling crack to his own mother, shooting his own brother, and letting his girl board a plane with his work. But each of the three verses unspools so poetically that the emotion of the stories transcends any lingering after-school-special undertones. —Al Shipley

DMX “Slippin” (1998)

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Producer: DJ Shok

Album: Flesh of My Flesh, Blood of My Blood

DMX confronted his own demons relentlessly on a series of blockbuster albums, until those troubles seemed to help send his career into a sharp decline. And when it came time to launch an album as a superstar for the first time with his sophomore effort, he used the lead single to put those inner conflicts on full display. Whether intentionally or not, the chorus of “Slippin’” seemed to mimic the catchphrase for the campy LifeCall medical alarm commercials (“I’ve fallen and I can’t get up!”), something that could’ve deflated the emotional impact of the track. Although it’s edited for curses due to issues with the sample, the autobiographical detail of the verses, particularly the surprisingly uplifting third verse, gives “Slippin’” a resonance beyond the usual DMX fireworks. —Al Shipley

Beanie Sigel “What Ya Life Like” (2000)

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Producer: Robert "Shim" Kirkland

Album: The Truth

Beanie Sigel came into the rap game with a rap sheet, and the State Property leader has been in and out of state facilities throughout his career. But he sounded as grizzled and wizened about the harsh realities of life on the wrong side of the law as he could possibly get even on his debut album, and the highlight “What Ya Life Like” plays like a musical version of Scared Straight. Where jail time sometimes gets shrugged at in gangsta rap like an acceptable inevitability, Beans leans into dramatic, evocative descriptions of solitary confinement and drug smuggling behind bars with jaw-dropping intensity. —Al Shipley

Eminem “Cleanin' Out My Closet” (2002)

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Producer: Jeff Bass, Eminem

Album: The Eminem Show

No rapper has ever aired out more of his dirty laundry before a bigger audience than Eminem, much of it dealing with his troubled relationships with both his mother and his baby mama. And while most of his biggest hits and most memorable songs were comical or high concept, “Cleanin’ Out My Closet” was the moment in his run of monster hits that spilled all of his family business out onto the Top 10 of Billboard. Sure, he had vented about his mother many times, but never for a full song and never with as much clear-cut detail as, “Just try to envision, witnessing your momma popping prescription pills in the kitchen,” and “Remember when Ronnie died and you said you wished it was me?”

It may sound like Em’s last word to his mother, closing the book on any possible reconciliation, but then his recent single “Headlights” revisited the subject with a more tender perspective and a disowning of this song with, “I no longer play at shows and I cringe every time it's on the radio.” —Al Shipley

Nas “Last Real Nigga Alive” (2002)

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Producer: Ron Browz

Album: God's Son

A year after “Ether,” Nas reunited with the landmark diss track’s producer, Ron Browz, for a far more introspective and ambivalent look at the events that led up to Esco’s conflict with Jay Z. In the course of addressing that, however, the often secretive MC pulled back the curtain on a number of other issues, including his less public tensions with Biggie and Raekwon, time spent with his ailing mother during his long hiatus between albums, and the woman he and Jay had in common. The song ultimately represented a minor chapter in the war and eventual truce between Nas and Jay Z, but it was also a rare moment when one of the two opponents spent more time explaining his personal history than simply using it as ammo. —Al Shipley

50 Cent “Many Men” (2003)

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Producer: Digga, Luis Resto, Eminem

Album: Get Rich or Die Tryin'

The nine gunshots that 50 Cent took before his ascent to superstardom are an indelible piece of both his music and his image. It provided him both a harrowing backstory, and taking a bullet to the jaw actually improved his delivery. But he never wrote as vividly about the actual experience as he did on “Many Men (Wish Death).” At times, the song is the defiant roar of an unlikely survivor, sneering to his contract killer, “Go on and get your refund, motherfucker, I ain’t dead.” But even the blander lines like “Joy wouldn’t feel so good if it wasn’t for pain” carry a weight that they wouldn’t if 50 Cent hadn’t already experienced a kind of pain that few live to talk about. —Al Shipley

T.I. “I Still Luv You” (2003)

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Producer: Nick “Fury” Loftin

Album: Trap Muzik

Before the fame and before his marriage to Tiny Cottle, Clifford “T.I.” Harris had two children with his girlfriend since high school, Lashon Dixon…and a third child by another woman while they were still together. The first verse of “I Still Luv You,” addressed to Dixon, is an emotionally complicated account of that tangled soap opera. The second is addressed to T.I.’s absentee father. Those two threads are tied together by the third verse, in which Tip worries about reliving his father’s mistakes, and attempts to take responsibility for his actions and make the best of his unplanned parenthood. Last year, Tip explained to us the song was made when his father was dying: “We spent his last days together. I made that song to let him know that all is forgiven.” —Al Shipley

Gucci Mane “Worst Enemy” (2009)

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Producer: Drumma Boy

Album: The State vs. Radric David

Gucci Mane is better known for loopy descriptions of lavish living than lyrical introspection. But at the height of his career, when his legal troubles landed him back in jail just as his Warner Bros. debut was being released, Gucci found himsel in an especially reflective mood. By addressing his personal setbacks and his beefs with Young Jeezy and T.I. on "Worst Enemy," Gucci took responsibility for his actions, even taking an apologetic tone at times (“I dissed Tiny, she didn’t deserve it”). But he also used the track to put himself in the pantheon of hip-hop troublemakers like 2Pac and Biggie, and hinted that his aggressive side wasn’t going anywhere. —Al Shipley

J. Cole “Breakdown” (2011)

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Producer: J. Cole

Album: Cole World: The Sideline Story

One of the new generation’s more sensitive rappers, J. Cole let the tears flow on this track from his major label debut. Often, he’s put on the middle class flip-side of more street-oriented rappers, but on “Breakdown” he digs into how things like addiction have touched his own life: “That shit these rappers kick is nothing like real life/You made a milli off of serving white? Yeah right/ My mama tell you what addicted to that pipe feel like.” —Al Shipley

Ab-Soul “The Book of Soul” (2012)

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Producer: Tommy Black

Album: Control System

Ab-Soul’s breakthrough album for Top Dawg Entertainment was released less than 3 months after the suicide of his longtime girlfriend Alori Joh. The final song recorded for Control System, addressed to her, became the album’s centerpiece. Soul details the debilitating struggles with Stevens-Johnson syndrome that haunted his adolescence, his youthful friendship and then relationship with Joh, and his plans to find her again in the afterlife. His voice rises with intensity, but he never loses his grip on the song’s intricate lyrics, resolving at the end of the track, “I ain’t finna stage a cry in this rhyme.” —Al Shipley

Drake “Look What You've Done” (2011)

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Producer: Chase N. Cashe, Noah “40” Shebib

Album: Take Care

Drake has a reputation for revealing lyrics that drop the usual bravado of hip-hop in favor of emotion and vulnerability. And he may have never put more of himself out there than he did on “Look What You’ve Done,” a down tempo Take Care cut with tender words for his mother and grandmother and how they helped him get to where he is now. When he gets to talking about one member of the family he didn’t see as much, he tries to shrug it off: “Damn, boo hoo, sad story, black American dad story.” But in that very uncommon moment of trying to mock and reject an emotional moment, Drake ends up revealing more about his feelings than if he’d just remained unguarded. —Al Shipley

Clipse f/ Jadakiss, Styles P, & Roscoe P. Coldchain “I'm Not You” (2002)

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Producer: The Neptunes

Album: Lord Willin'

Although each rapper did their thing on this song, please direct your focus to Malice's verse. One thing that separated Clipse from other cocaine rappers was the duo's ability to show the other side of hustling instead of just glorifying it. Malice openly expressed disdain for pushing poison to his community. Lines like, "Give this regret and sympathy to the streets/I seen them pay for their fix when their kids couldn't eat," are a chilling example of the demons drug dealers fight on a daily basis. These references to his past life are maybe part of the reason why he found God, changed his stage name to No Malice, and refrained from rapping about negativity. —Angel Diaz

Danny Brown “Torture” (2013)

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Producer: Oh No

Album: Old

Wildness aside, Danny Brown is one of hip-hop's most honest artists today. "Torture" details his horrific upbringing in Detroit with precise detail. He recalls seeing people shot in the head, watching one fiend beat another with a hammer, and witnessing another fiend burn his top lip trying to light up a crack pipe on a stove. Fast forward to today and you start to understand why Danny pops pills and sips lean just to get some sleep; he once told Complex, "No matter where I’m at, I can still close my eyes and see baseheads." This song (and the rest of the first half of Old) conjures early Danny Brown and reminds the listener that there's more to the MC than drugs and partying. —Angel Diaz

Royce Da 5'9 “Shake This” (2009)

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Producer: DJ Premier

Album: Street Hop

Royce Da 5’9” had a promising start to his career in the late ‘90s but things went astray. He started out rhyming alongside Eminem and ghostwriting for Dr. Dre but after his 2002 debut album, Rock City, failed to really take off, he succumbed to alcoholism in the mid-2000s as his relevance in rap declined. In an interview with Complex he discussed the rough patch in his life saying, “I was [in an] abusive period. I pulverized bottles.” His decline hit its nadir in 2006 when he was sentenced to a year in prison for a DUI.

He aired out all his shortcomings on the DJ Premier produced “Shake This,” a song where Royce wails, “Somebody come help me!/Find my strength to stop drinking this poison, 'fore I drown my gift.” But what made the track so harrowing was how he rapped about both his personal and professional life: “I gotta shake this jail shit off me/He ain't gon' never sell, he gon' fail shit off me.” Since that song, he's done just that by reconciling with Eminem and reforming their duo, Bad Meets Evil, to release Hell: The Sequel and earn his first gold plaque. —Insanul Ahmed

Kid Cudi “All Along” (2010)

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Producer: Emile

Album: Man on the Moon II: The Legend of Mr. Rager

Although some of his major hits have been uplifting, the hallmark of Kid Cudi’s style has always been dark anthems for lonely stoners. “All Along” might be the darkest song he’s ever made, the kind of thing you play when you've tried and failed so many times you’d rather go home and be alone than try again. The song’s producer Emile once told Complex, “I don’t think Cudi likes to talk about that record that much because it’s a personal thing for him.” The verses are short, with long gaps between lines, but the lyrics are haunting and the beat is as hollow as you imagine Cudi's life probably felt when he wrote the song. If you’re familiar with his work​, it’s no surprise to hear Cudi say, “I guess I’m meant to be alone.” —Insanul Ahmed

Game f/ Busta Rhymes “Doctor's Advocate” (2006)

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Producer: J.R. Rotem

Album: Doctor's Advocate

Game is one of rap’s greatest flip floppers. One minute he hates 50 Cent, the next he says he wants to reconcile with him; one minute he’s calling Jay Z his idol, the next he’s dissing him for no apparent reason. All the back and forth can make it hard to take Game seriously. But the one thing that’s always been constant for the MC is his love and admiration for his mentor Dr. Dre.

Still, by the time his second album was on the way, he'd been kicked out of G-Unit, shipped from Aftermath to Interscope, and fallen out of the good graces of the Doc. Despite that drama, the album’s title track was a heartfelt open letter to Dre. Game held nothing back, admitting “I betrayed you” and “I never said thank you, and I took it for granted.” For once, Game’s words held real resonance. The song worked, too; not only was Game’s second album a success but he eventually squashed the beef and worked with Dre again. —Insanul Ahmed

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