ap is the music version of gumbo. From the sour socio-political food-for-thought of dead.prez to the fight-instigating, adrenaline-pumping spices of M.O.P; and the soul-stirring potpourri of Kanye West—it’s all in the mix. I mean…in what other genre can an artist segue from cop-killer lyrics to spouting unabashed sentiment for his mama on the same album (sometimes in the same song)? But way before a disoriented Andre 3000 adorned purple pants and belted out “Pink & Blue” in his most manly voice, hip-hop had reluctantly divulged a plethora of sentimental tunes. We, at Stylus, have documented those golden days. So, sit back, relax, and turn off the lights as we run our finicky fingers through rap’s Sentimental Songs catalog.

10. Will Smith – Just the Two of Us
Although the jury is still out on whether Will Smith should be categorized as a rapper at all, there’s no denying the snazzy sentiment in this song. Will tramps on a field most rappers are too scared (or too macho) to tread on, pledging dignity and loyalty to his lil’ man. And, he does it over a tune we know so well.

09. Fall-N-Love – Slum Village
Sick and tired of reprimanding sellout rappers the old-fashioned way, T3 and his crew of loosely-associated cronies resort to sentiment. A low-scale ominous beat plays the backdrop for SV’s spiel, reminding us why we fell in love with Villa in the first place.

08. Eminem – Stan
Eminem is easily the most sentimental rapper ever (if only hip-hop purists would resist fisticuffs over such a categorization). Stan is the ill-fated account of a psychotic fan, who dreams of sodomizing his favorite rapper. Dido’s ethereal crooning adds more soot to the song.

07. Jay-Z - Song Cry
Just when you thought Hov was all about money, cash, hoes (actually he is), he pulls out his storytelling hat and struts a classic rap love song. Although, Jigga’s defiant attitude is alive here (instead of shedding the tears himself, he makes the song cry), he’s sentimental enough to concede being called ‘ugly’ by the female in the story.

06. De La Soul - Eye Know
This seminal jazzyfied hip-hop crew was the first to rhyme about daisies and dames and make it sound, oh so sweeeet. Long before Ja Rule and others tarnished the concept of sentimental rap, De La’s candy-coated musings over lush soulful samples made it noble to declare sweet affection for that special person—be it your spouse, mom, or the nanny!

05. A Tribe Called Quest – Bonita Applebum
Over the sound bed that later became a sonic playground for The Fugees’ 1996 remix of Roberta Flack’s “Killing Me Softly,” ATCQ romanticize a calm, yet thumping drumbeat. With his nasal flow and soothing delivery, Q-Tip never raises his voice, masterfully pausing between lines for ardor. A hip-hop version of Quiet Storm.

04. Mos Def/DJ Honda – Travellin’ Man
Traveling all the way from Japan to the USA, DJ Honda dismantles a gritty sonic template and rebuilds it using funky jazz fragments. The result is a lush mix of harmonic samples and a cool street hip-hop drum track. Mos takes advantage of the shimmering production, seamlessly seesawing between rapping and singing about the journey that is Life.

03. Ghostface feat. Mary J. Blige – All That I Got Is You
Who knew that the man that once claimed to “bite the nose off” and swore “if you don’t bring me the muthafuckin’ Cognac, I’ll kill you” had a soft spot for something. Ditching the usual 32 bars strata for a long-running verse, Ghostface unleashes genuinely emotional lyrics about crashing in a congested apartment with his mom, drinking sugar water, and plucking roaches out of cereal boxes. No hard-hitting drums, no anti-swine-eating vignettes. Just Mary J. Blige’s tear-jerk crooning and Poppa Wu’s solemn words of wisdom at the end.

02. Pete Rock and CL Smooth - They Reminisce Over You [T.R.O.Y.]
Insane horn riffs, shimmering cymbal flares, soulful samples, you just know it’s Pete Rock’s unmistakable craftsmanship. CL Smooth channels controlled emotions through the mic on this funeral favorite. Even though, CL swears he’s “noddin’ off, sleep to a jazz tune,” this is melancholy elegy at its finest.

01. 2Pac – Dear Mama
It was ‘Pac who made it cool for rappers to eulogize mothers in the 90’s. In a meticulously-crafted song that reveals the late icon’s softer side, 2Pac pats his mom on the back for attempting to liberate him life on the street. Heart-wrenching emotions and poignant lyrics make “Dear Mama” a sentimental hip-hop masterpiece.