Deeper Than Rap: 40 Heartfelt Hip-Hop Songs

By 03.15.12

Hip-Hop gets such a bad rep sometimes. Go ask any group of random people what they think about the constantly-evolving genre and you’ll undoubtedly hear half the answers harping on how endangering such reckless noise can be for our youth. But, the truth is most of those crusty old blame-shifters probably haven’t heard anything more than a few Slim Shady singles and are just as ignorant as the songs they speak of.

In an effort to show folks Hip-Hop is much more than a scapegoat, here are 40 songs that put the heart of rhyming on full display and remind one-sided MCs they need to expand beyond drugs, woman and violence if they want call themselves a complete artist.

1. Common Feat. Lauryn Hill – “Retrospect Of Life”

Before Common was acting or No ID was producing the biggest Hip-Hop records on the planet, the Windy City duo hooked up to help fathers-to-be make the right decision about their potential babies. The song features Lauryn Hill, during her prime nonetheless, who also happened to direct the music video for this One Day It’ll All Make Sense single.

2. T.I. Feat. Jamie Foxx – “Live In The Sky”

One of the more sentimental songs of Clifford Harris’s career is this piano-laced gem from his KING album, which found the Bankhead rapper wishing his fallen loved ones well on their long journey ahead. Unfortunately though, TIP’s life only got rockier after this was released. Not long after the video was shot, his close homie Big Phil was murdered following an altercation at a nightclub, which set up a chain of events that altered the Grand Hustler’s life forever.

3. Fort Minor Feat. Holly Brook – “Where’d You Go”

You may or may not remember when Linkin Park’s lead man, Mike Shinoda, stopped beating around the bush and went all-out Hip-Hop as the front-man for Fort Minor. Well, if you do, it’s probably because of this successful single, which is dedicated to the person left behind in long distance relationships. Oh Face Time, how you’ve changed the world.

4. Ed O.G. & Da Bulldogs – “Love Comes & Goes”

On this somber single from Edo G’s 1993 album Roxbury 02119, the Boston MC breaks down three different tragedies that disrupted his own life and unfairly sent aftershocks through the family members of those fallen friends.

5. Saigon – “Oh Yeah (Our Babies)”

Turn on the news in any city – small or large – and you’ll see kids dabbling in dirt earlier and earlier in age. It’s quite disturbing, but has unfortunately become a twisted fact of life. As someone who’s seen these tragedies first hand from multiple points of view, The Yardfather dissects the affects of this ongoing epidemic on this epic chapter from The Greatest Story Never Told.

6. Lil Wayne – “Something You Forgot”

Something a lot of people forget is that Weezy actually has some substance once in a while, which is on full display throughout this track from the Carter 3 sessions, where he laments over a lady lost. Some say it’s Trina, but we just say it goes deep and appreciate when he allows that vivid mind to differentiate from the norm.

7. Twista Feat. Faith Evans – “Hope”

When Kamikaze dropped in 2004, there were some people who felt this uplifting cover-all was somewhat cheesy. But, what could possibly be wrong with wanting DOC to speak again or wishing “the super-homie Christopher Reeve could still walk”? Nothing. That’s what.

8. J. Cole – “Lost Ones”

Three years and two releases after Cole wrote and let loose this three-sided tale of abortion back in 2009, this deep cut from The Warm Up still stands among the Roc Boy’s best.

9. Proof – “Kurt Kobain”

This final letter from the late Mayor of Detroit Hip-Hop is unique, in the fact it probably wouldn’t have been as moving had Proof not passed. But, when he did, this highlight from his Searching For Jerry Garcia album became both the crown jewel of his catalogue and a way for mourning fans to see-off the MC known for leaving a lasting impression. We wish you could take it back too, homie.

10. Atmosphere – “Yesterday”

The renowned duo of Slug & Ant named their sixth album When Life Gives You Lemons, Paint That Shit Gold, which couldn’t have been exemplified better than here. If you haven’t heard this soulful track before, there’s a good chance you’ll listen to Slug spit almost the entire song and not know who he’s talking about, until a gut-checking final detail is let loose in the last bars and pulls your heart out.

11. Raekwon – “Ason Jones”

No one quite knew how the typically-rugged Wu collective would handle the passing of their beloved ODB. But, when Raekwon dropped the much-hyped and critically-acclaimed OB4CL2 a few years back, The Chef reached into a special place in his kitchen and rewound the good times with this dedication to Dirt McGirt.

12. Flipsyde – “Happy Birthday”

Another ode to the unborn, this specific single is from the somewhat-forgotten Oakland group’s We The People debut in 2005, and may have been a precursor of sorts to the letters The Throne would write years later. If you’ve ever been through a similar situation, this one has to be extremely hard to hear.

13. Game – “Never Be Friends”

Before he was with G-Unit and had his own sneaker line, the Game was making his name known from reality raps like this dedication to his fallen homie Billboard. The toughest part about hearing Chuck rock the RIP blues is that you can tell he partially blames himself.

14. Beanie Sigel Feat. Scarface – “Mom Praying”

If you’ve been having a rough go, one way to know you’re not alone is throwing on this open door to the worn organs of Broadstreet Bully and Scarface. Substituting the therapist with a soulfully systematic Just Blaze beat, these two tough-skinned MCs exercise their deepest family issues on this cut from Beans’ The Reason.

15. Don Trip – “Letter To My Son”

The newest addition to this list is the riveting tale of Memphis MC Don Trip’s continual fight to regain custody of his son, which is so upfront and touching, it’s become one of the better singles to come from Hip-Hop in years.

16. Haystak – “Still You Doubted Me”

This under-the-radar entry from Stak Mak is for all the people out there who’ve continually been told again and again they’re not good enough. If you can’t feel the Nashville resident’s soul spilling onto this track, you may want to check your pulse.

17. Big Sean – “Memories Pt. II”

Considering how much Big Sean has evolved into the mainstream since the original version of this record came out on the Detroiter’s Finally Famous 3 mixtape, his humble wavering on display here almost seems like an afterthought. But, what sticks is the line about Sean losing touch with his best friend after he became addicted to pain pills, which is a problem becoming more and more prevalent in our current RX-fueled society.

18. Slaughterhouse – “Rain Drops”

While each of the four members of Shady’s sole supergroup could’ve made this list on his own steam, this Grand-Canyon-deep cut from Slaughterhouse’s debut LP showed they can release their pent-up aggression as a unit as well as they can solo dolo.

19. Killer Mike – “You Don’t Want This Life”

For all the flaunting influential rappers do with their earnings, it’s not surprising half the youths these days aspire to mimic the lifestyles of their radio idols. However, on this choice bonus cut from Killer Kill’s I Pledge Allegiance To The Grind, ATL’s underground king explains why the lifestyle of a hustler isn’t for everyone.

20. Bizzy Bone – “Nobody Can Stop Me”

Aside from the fury of patented fast-flows on display during his Heavenz Movie debut, this unraveling single found Bone’s most sought-after member letting listeners in on some of his deepest secrets, which might explain some of the issues and antics later in his career.

21. Lil Boosie – “Holding On”

Although the beat is a bit more amped than most features on this list, Boosie’s continual trials and tribulations are no more evident than on this emotional roller-coaster from the Gone Till December mixtape the Trill headliner released in 2010. Unfortunately, things only got worse from there.

22. Jay-Z – “Song Cry”

We know a lot of the ‘fellas will pretend they can’t relate to the lamented love on display during the final single from Hovito’s Blueprint. But, every guy’s got at least one chick that got away and this is Hip-Hop’s dedication to her.

23. Mac Miller – “Poppy”

Despite still being just one of the K.I.D.S. on his breakout mixtape from 2010, the then-19-year-old Pittsburgh rapper coped well with the loss of his grandfather by dedicating this jam to the man who used to walk him to school.

24. DJ Quik Feat. El Debarge– “50 Ways” (Original Version)

“They tell me Quik, suck it up, like I’m supposed to…but me & Mausberg were closer than most knew.”

When DJ Quik found out his 21-year-old apprentice Mausberg had been gunned down on July 4th, 2000, it affected him more than people realize. This Paul Simon-sampling ode to his homie finds the Compton composer contemplating 50 ways to get over the tragedy.

25. Lupe Fiasco – “He Say, She Say”

This taste of Food & Liquor finds the leader of the Lasers depicting a first-hand story of a mother & son combo vying for a father figure in their lives, which unfortunately can be easier said than done in many situations.

26. Z-Ro – “Look What You Did To Me”

When all your life consists of is D’Evils, who else can you turn to but a preacher? Well, on this throwback track from one of Houston’s most troubled rappers, the King Of The Ghetto emotes in the confessional about trying to turn his life around. Considering this track is now 14 years old and Ro’s past four albums have been named after the four hardest drugs known to man, we’ll assume he’s still fighting those demons.

27. Notorious B.I.G. Feat. 112 – “Miss U”

Going into anything after “Notorious Thugs” is a tough task, but on Life After Death’s second disc, Biggie succeeds with a first-hand recollection of three different lost loved ones. The song furthered Chris Wallace’s sensitive side and proved to be just another slice of unfortunate irony from Hip-Hop’s ultimate farewell LP.

28. Ghostface Killah Feat. Mary J. Blige – “All That I Got Is You”

The motion picture mind of Wu-Tang’s flashiest member isn’t just limited to orchestrating elaborate black market masterpieces. Actually, the first mainstream single Tony Starks released in 1996 was this Mary J-assisted dedication to the woman who raised him.

29. Eminem – “When I’m Gone”

Amidst one of the darkest periods of his life, a more & more reclusive Marshall Mathers shared his inner-grief with listeners on this original song from Curtain Call: The Hits in 2005, depicting how the logistics of celebrity status strangle his family ties with 1080p imagery.

30. Big K.R.I.T. – “I Gotta’ Stay”

Throughout his relatively short time in the spotlight, one of the main themes behind Big Krizzle’s open book is the undying love for his deceased grandmother. Her influence obviously left a lasting impression on the MS rapper and this sentimental slow flow from his Krit Wuz Here project was the first of many times fans would hear him reaching out to her on wax.

31. Nelly – “Luven Me”

Everyone’s driven his or her mom crazy at one point or another and to close out his Country Grammar debut, the lead St. Lunatic penned this apology of sorts, unveiling a softer side he would end up embracing later in his career.

32. Pete Rock & CL Smooth – “T.R.O.Y.”

When Mt. Vernon’s favorite duo wrote this tribute to their fallen friend T.Roy, they surely had no idea it would eventually became the Hip-Hop classic it is today, let alone one of our current first lady’s favorite songs. Talk about a legacy.

33. Bone Thugs-N-Harmony – “Crossroads” (Remix)

This list wouldn’t have been complete without a shout out to Wish Bone’s uncle Charles, from Bone Thugs’ revered E. 1999 remix.

34. Nas – “Dance”

After a highly-publicized feud with a fellow NY comrade rebooted his career, Nasir Jones capitalized with a string of critically-acclaimed LPs in Stillmatic, The Lost Tapes & God’s Son over the next two years. The last of those three featured the Queens revolutionary breaking hearts with this last request to hit the floor with his mother, who passed during the LP’s creation.

35. UGK Feat. 3-2 & Ron Isley– “One Day”

This opener to the Underground Kangz’ Ridin Dirty set the tone for the Port Austin duo’s most complete LP, by delivering a touching, guitar-laden reminder that your scripts can be flipped in an instant.

36. Master P Feat. Silkk the Shocker, Sons of Funk & Pimp C– “I Miss My Homies”

At the peak of his success, Percy Miller funneled frustration from the death of his brother Kevin into a Billboard success story. Amidst Ghetto D’s mix of substance abuse and rap marginalization, this Beats By The Pound-produced gut-check still stands the test of time.

37. Drake – “Look What You’ve Done”

By the time Take Care came out last year, Drizzy’s success was higher than ever. In an attempt to bring that come-up full circle and simultaneously relate to listeners, the Young Money superstar showed how a tumultuous parental upbringing helped set-up his currently emotional style.

38. Dr. Dre – “The Message”

Hip-Hop folklore (aka the highest rated YouTube comment) claims Nickel Nine was the writer of this sonic honoring of Dre’s brother Tyree from Chronic 2001, which was produced by Lord Finesse. But, no matter who guided the good Doc’s tribute, this harp-heavy head-hanger was a solid closer to his classic second LP.

39. Kanye West – “Family Business”

No one has a perfect family tree. Each and every one of us has blood relatives who’ve been through the ringer and back, stirred up group gatherings with their shenanigans or made bad decisions that you’ve had to undoubtedly had to forgive in the long run. To round out College Dropout, Yeezy toasted to looking past personal hang-ups with unwavering love with this new school classic.

40. 2Pac – “Unconditional Love”

Realistically, half of 2Pac’s catalogue could’ve made this list. When he wasn’t thugging it up in the studio, the late legend made music that touched the masses, making him maybe the most versatile artist Hip-Hop has ever seen. So, instead of limiting his reach to just mothers (“Dear Mama”) or the fallen soldiers (“Life Goes On”), we’ll spread the Thug Angel’s love to everyone, with this gem from his certified-diamond Greatest Hits album.

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