You’ve likely seen a lot going around the last week or so about the 50th anniversary of hip-hop. It’s quite the milestone for a genre that has almost taken over as arguably the most popular genre of music today. It’s gone from underground to mainstream to a cultural revelation, spinning off sub-genres, rappers-turned-actors, and has truly shaped the landscape of that the 90s, 00s, and so on have become.
As a child of the 90s, I was lucky to catch the wave as the genre took to the mainstream. Dr. Dre, Snoop, Em, Puff, 2Pac, Biggie… all of them helped shape and mold. With that, I present to you my ode to 50 years of hip-hop. These 50 songs helped shape me and are 50 of my favorite songs from the genre. These are purely based on me, myself, and I. I’m not claiming these are the best songs ever of the genre, but these are the songs that hit hardest for me and impacted me the most. A few newer, most older, cloaked in 90s nostalgia and greatness.
So let us gather ‘round and toast to the genre that continues to grow and shapeshift. While my tastes in the genre has shifted to more “alt hip-hop”, I am grateful for the growth of the genre and excited for the next 50.
50. Bun B “Get Throwed”
Album (Year): Trill (2005)
Port A, stand up! Bun is a true OG for any Houston kid, and the legend made sure to hit it right with features from UGK partner Pimp C, Z-Ro, Jay-Z, and Jeezy.
49. Raekwon “Guillotine”
Album (Year): Only Built 4 Cuban Linx... (1995)
Wu-Tangs own Raekwon went hard on his debut album with “Guillotine”, getting fellow Wu members Ghostface Killah, GZA, and the oft slept on Inspectah Deck. 4:22 of pure Wu but without the actual Wu.
48. Reflection Eternal “Ballad of the Black Gold”
Album (Year): Revolutions Per Minute (2010)
Talib Kweli and Hi-Tek absolutely went off with their 2010 collab album under the moniker Reflection Eternal. There was a good two year period where this album did not leave my car, and “Ballad” was a big reason for that.
47. LL Cool J “Shut ‘Em Down”
Album (Year): Any Given Sunday OST (2000)
“Mama” is truly the pinnacle of LL’s catalog, but “Shut ‘Em Down” was the epitome of cool to a freshman high schooler. The flow, the feel, just everything about the song rules.
46. Jay Electronica “Shiny Suit Theory”
Label (Year): A Written Testimony (2020)
More to come from Jay Elec, but “Shiny” carried me through the pandemic (really the entire album) and you add in The-Dream and Jay-Z into an already catchy beat, you’ve caught fire. Jay Elec truly one of a kind.
45. Benny The Butcher “Johnny P’s Caddy”
Album (Year): Tana Talk 4 (2022)
One of the newest songs on this list, but all I can say is Benny and J. Cole did not have to go this hard for us but they did. I made a friend with my Uber driver going to the airport when he was blasting this at 7am and I started talking about Benny and Freddie’s beef, and how good this song is. Street cred came in bunches!
44. Busta Rhymes “Break Ya Neck”
Album (Year): Genesis (2001)
A bop. That intro just makes you want to bob and move. Busta one of the most slept on of our generation and i’ll take that to my grave.
43. Biz Markie “Just a Friend”
Album (Year): The Biz Never Sleeps (1989)
YOOOOOOUU…. YOU GOT WHAT I NEED. Iconic.
42. Kota the Friend “Alkaline”
Album (Year): Foto (2019)
Kota is one of the better up-and-comers in the alt hip-hop scene, and the whole Foto album lives up to something special. “Alkaline” takes the cake, though, and can be spun over and over and over and ov…
41. Petey Pablo “Raise Up”
Album (Year): Diary of a Sinner: 1st Entry (2001)
North Carolina, raise up! Try listening to this song without singing “twist it like a helicopter”. It’s not possible.
40. Bone Thugs-N-Harmony “The Crossroads”
Album (Year): E. 1999 Eternal (1995)
A dedication to Eazy-E, this is one of the most important songs of the genre. Take a listen to the lyrics and let it overtake you, simply put.
39. Point Blank “Born and Raised in the Ghetto”
Album (Year): Self-Titled (2008)
College me loved this song. No idea how it got in my hands, but i’m so thankful these Toranto cats found their way to me. It also introduced me to Phyllis Dillon with their great sample use, so there is that, too.
38. Wu-Tang Clan “Gravel Pit”
Label (Year): The W (2000)
“C.R.E.A.M.” is great and more iconic. But it was “Gravel Pit” that got me into Wu and allowed me to explore the back catalog as a kid. Plus, a sweet James Brown sample goes a long way for me… as you’ll see (again) later down the list…
37. P.O.S “P.O.S. Is Ruining My Life”
Album (Year): Audition (2006)
P.O.S is one of my favorite hip-hoppers of all time, even with his troubles and his #metoo moment (which he has owned.. not right but I do respect the ownership), and this is the song that started it all for me.
Sampling Underøath, the scene kid I was in ‘06 got hooked. Not to mention, it was him + Atmosphere that turned me on to Rhymesayers and the Doomtree collective, which i’m forever grateful for. This song, in particular, is just crunchy as f**k and a hellava good song blending hip hop, emo/screamo into something new and fresh before 10+ years before emotrap and emo rap became suddently mainstream with Juice Wrld, Peep, et al.
36. J. Cole “No Role Modelz”
Album (Year): 2014 Forest Hills Drive (2014)
First things first rest in peace Uncle Phil. The best opening line of any song, ever. Cole is one of the realest in the mainstream game today, and this is the best off a fantastic, modern-day iconic album.
35. Big K.R.I.T. “Country Shit”
Album (Year): K.R.I.T. Wuz Here (2010)
K.R.I.T. was (and is) it. Underrated beyond measure, and a true southern hip-hop staple in the mid 00s with his mixtapes. This song is hard to beat from top to bottom. Third ward, muddy water stand up.
And a little trivia: the music video has a cameo from Chamillionaire. Bet ya haven’t thought of that name in a hot minute..
34. Eminem “‘97 Bonnie & Clyde”
Album (Year): The Slim Shady LP (1999)
Shady brought dark rap/black humor to the mainstream. At the time, this song was as dark as you can get - and while our world has changed, the impact hearing this back in ‘99 had on middle school me is unchanged. Powerful, and a true masterclass in storytelling.
Em is a true heavyweight, and if we opened this to Top 100, we likely have more of Shady.
33. Childish Gambino “Bonfire”
Album (Year): Camp (2011)
Heavy beat, a perfect intro for Donald into the Gambino moniker. If you can drop a ToeJam and Earl reference, you make my list.
32. OutKast “Rosa Parks”
Album (Year): Aquemini (1998)
Hush that fuss, y’all. Iconic, and the song the set OutKast on the icon trail two years before they drop their greatest piece of commercial work.
31. Snoop Dogg “Lay Low”
Album (Year): The Last Meal (2000)
Snoop is likely best known for “Gin & Juice” (a fantastic song) and some of his later hits that became party staples (“Young, Wild and Free”, “Drop It Like It’s Hot”), but “Lay Low” is a sleeper hit when looking at Doggs body of work. Peaking at no.5 on the Billboard Rap charts, the song is quintessential west coast… with features from Nate Dogg, The Eastsidaz, Master P, and produced by Dre. Plus, the video is mafia themed… what more can you want?
30. The Weeknd “The Zone”
Album (Year): Thursday (2011)
The Weeknd may be a full-fledged headliner pop staple now, but his trilogy of albums to start his career were absolutely perfect and groundbreaking. A wildly brilliant blend of hip-hop, R&B, pop. And “The Zone” tops that list… an absolute banger, and a nice feature from Wheelchair Jimmy.
29. Sol “2020”
Album (Year): Yours Truly (2012)
Seattle rapper Sol dropped one of the best albums of 2012 in Yours Truly, and “2020” was the clear banger of the bunch for the PNW underground heat-seeker.
You got that Jesus on your chain while you do nothing but party.
28. Mac Miller “Kool Aid & Frozen Pizza”
Album (Year): K.I.D.S. (2010)
RIP Mac. The first song I heard of his, and the song that stayed with me the longest through his incredible catalog. Nostalgic, fresh, and a moment in time that can be recalled by anyone who loved their childhood. Thank you, Mac.
27. The Sugarhill Gang “Jump On It”
Album (Year): 8th Wonder (1981)
The godfathers of rap and hip-hop dropped “Rapper’s Delight” a year prior, but it was “Jump On It” that followed and was an absolute banger. From The Fresh Prince to everything in between, the song is just so iconic. Try not to move when you hear it, Carlton.
26. OutKast “B.O.B.”
Album (Year): Stankonia (2000)
While “Rosa Parks” put OutKast on solid footing as ATL ‘ones to watch’, it was the entire Stankonia album that made them legends in their own right. So many hits and great songs, but it is “B.O.B.” that resonated the most - and is truly one of their most iconic songs in an absolutely stacked catalog.
25. Coolio “Gangsta’s Paradise”
Album (Year): Gangsta’s Paradise (1995)
RIP Coolio, we lost a great one. While Coolio had a few other medium to minor hits, “Gangsta’s Paradise” was one of the biggest rap hits of all time. If you can snag Michelle Pfeiffer at the height of her career and get spun into “Amish Paradise” by Weird Al, you’ve made it. Ahhhhh here we goooooo.
24. Jay-Z “Big Pimpin’”
Album (Year): Vol 3… Life and Times of S. Carter (1999)
Hova dropping in with the help on Bun B and Pimp C. “Big Pimpin’” had every middle school/high school kid thinking the song was about them, and every gangster ready to climb aboard a yacht. It’s addicting, it’s smooth, and 20+ years later, the song still holds up so well.
23. Kanye West “Jesus Walks”
Album (Year): The College Dropout (2004)
Before the man went crazy and became a tabloid staple, Ye released a string of albums that went nearly unmatched in the hip-hop world. His debut being The College Dropout, which enlisted a track-listing so strong, it’s hard to imagine another artist doing something similar today. But it was “Jesus Walks” that changed the game.
It was poignant, it was new, and it had never been done before in this light. 808s is still his best work in my eyes, but the first three albums are nearly perfect with the cerise sur le gâteau being “Jesus Walks” and that one song he did with Chris Martin (lol).
22. Saba “PROM / KING”
Album (Year): Care For Me (2018)
Honest and heartbreaking is the best way to describe Chicago’s native son Saba’s song “PROM / KING”. Dealing with the death of his cousin, it’s a journey leading up to his death and what took place. Perfectly written, perfectly honest, and brutally raw. Storytelling in the A+ echelon.
21. Frank Ocean “Novacane”
Album (Year): Nostalgia, Ultra (2011)
Nostalgia was a game changer. Many a mixtapes caught the attention of the fans in the late 90s and into the aughts, but none gripped the nation or set the artist up for cult status/launching a career like Nostalgia did for Frank.
While many of the songs sampled were fresh and new, it was “Novacane” and “Swim Good” that took the cake. Either one could fit in this 21 slot, but “Novacane” absolutely blew my mind the first 200 times I heard it. With the right pair of earphones, it can still blow my mind 10+ years later.
20. J. Cole “Villuminati”
Album (Year): Born Sinner (2013)
Cole World had been out for two years when J. dropped Born Sinner. With this release, he proved to everyone he had not overstayed his welcome as a major hip-hop player. If anything, this set up what was to come with 2014FHD and the born legend of Cole.
“Villuminati” is like a split personality, of riding the tightrope between finding success or selling out. I think Cole picked right staying fresh, new, and being himself, and “Villuminati” was a clear cookie cutter process of him figuring it out in real time in front of us. Brag like Hov, J.
19. Reflection Eternal “Lifting Off”
Album (Year): Revolutions Per Minute (2010)
Talib and Hi-Tek return to my list with “Lifting Off”, a song all about getting high. It’s catchy, it has a slick beat over the bubbling of a bong, and shows off Talib and his skillset as a rapper so well.
like the Mars rover or the weight on your shoulder
That held you down with the weight of a boulder
Whether a drug dealer baking the soda or a revolutionary soldier
I tried to buy LSD
But a dred refused to sell it to me
He was like, well yeah, I got it, but that's a white man drug
Not for us, I said aight man, love.
18. P.O.S “Let It Rattle”
Album (Year): Never Better (2009)
Doomtree great Lazerbeak made one hellava beat, and the live drums add to this song being wildly epic. Spit bars about Mitch Hedberg, reference The Big Lebowski numerous times, and 90s WWF wrestling, you got me. The perfect opener for his third album, and one of the best songs of the first decade of the new millennium.
Double, double eat up, ride, the Dude abides.
17. The Notorious B.I.G. “Mo Money Mo Problems”
Album (Year): Life After Death (1997)
I had “Juicy” on here at one point towards the 45-50 range, but it was ultimately the chopped & screwed version. You can take the kid out of Houston but…
Lo and behold, it got booted, but “Mo Money” reigns supreme in my Biggie playbook. The beat is so iconic. That guitar riff, the Diana Ross “I’m Coming Out” sample… just everything about it screams happiness and 90s hip-hop to me. Puffy, Mase, Biggie… the trinity of 90s east coast hip-hop.
16. Method Man & Redman “Da Rockwilder”
Album (Year): Blackout! (1999)
OOOOOHHHH MYYYY GOOOOOD.
Absolute spitfire. Clocking in at 2:16, the Wu duo (Red has often been called the 11th member, don’t @ me) just absolutely went off. There was supposedly two verses that each did, but it didn’t sound right and they cut it down to one verse each. Good move in my opinion, as what we have is pure perfection.
15. Benny the Butcher “5 to 50”
Album (Year): The Plugs I Met (2019)
The album closer for the absolutely perfect The Plugs I Met, something about this song just grabbed me years ago. So much so that this song constantly finds itself in my EOTY top played songs on Spotify. Benny certainly has a sound, but this is the crescendo of sound for Get Benny in my book. I mean, how is this not goals?
Check my bank statements, probably hurt your feelings
How I'm in every verse admittin'
How I work a kitchen like it's Church's Chicken
14. Jay-Z & Kanye West “N***** In Paris”
Album (Year): Watch the Throne (2011)
AKA “Fellas in Paris” to my wife and I, this whole album is truly epic and the stuff of legends. Supergroup of all supergroups. The second you hear that beat kick in at the :05 mark, you know you have something special.
It is so fresh and iconic, Hamburger Helper made an entire album based off WTT. To quote Jigga, “I am where art meets commercial. The sweet spot between the hood and Hollywood.” I listen to this song and cannot not think of that quote for both him and Ye as they go off.
Ball so hard.
13. Kevin Gates “2 Phones”
Album (Year): Islah (2016)
One of my biggest guilty pleasures of a song. Trap music on the come up in the mid 2010s, and this hits the heights of that era for me. Chorus is perfect. Verses are good, beat is a bit outdated at times, but dammit if the song just doesn’t do it for me when that chorus hits.
12. DMX “What’s My Name”
Album (Year): …And Then There Was X (1999)
RIP X. Back in my heyday of listening to more commercial-leaning hip-hop, I learned this song from start to back. 20+ years later, I know about 3/4 of it… growing up sucks.
Nevertheless, the song still slaps and the lyrics are fantastic, even if I must be culturally sensitive (and rightfully so) these days. For me, it’s the nasty hook and the anger X brought throughout his career and this song that goes nearly unmatched.
11. Rick Ross “Diced Pineapples”
Album (Year): God Forgives, I Don’t (2012)
Rozay. Wale. Drake. Try to write a song and combine the fruit, thug passion, and diamonds all under the umbrella of “pineapple” and come back to me. Wale verse is fire, and Drizzy hitting that chorus works so well over the piano loop. Drake can feature on songs all he wants and i’m good with it, but won’t ever find his body of work scratching my Top 100… (hot take)
10. Gang Starr “Moment of Truth”
Album (Year): Moment of Truth (1998)
One of the realest songs of the era. The beat is genius, the lyrics are relatable in most situations in life. We all have that moment of truth, and Gang expressed it so well during a time we all needed to hear it.
Actions have reactions, don't be quick to judge
You may not know the hardships people don't speak of
It's best to step back, and observe with couth
For we all must meet our moment of truth
9. Jay Rock “All My Life”
Album (Year): Follow Me Home (2008)
One of the songs that featured Kendrick before Kendrick was Kendrick. Jay Rock dropped this song in ‘08 which featured a chorus by an artist once known as K. Dot (Kendrick), but the song got a makeover two years later with features from Lil Wayne and will.i.am. Regardless of the version, this song absolutely goes hard. Still one of my favorite lines from any hip-hop song ever:
Black and white TV set, no cable
40's in the fridge, chicken noodles on the table
I wasn't born with a silver spoon
Child of the ghetto, raised off a different tune
Watching Bob Barker in my living room
If your price was right, I could get you a whole living room
8. Ice Cube “It Was a Good Day”
Album (Year): The Predator (1992)
Not only is it important to know that Cube’s good day was 1/20/92, but it’s important to know how iconic this song is and how it help spur along Cube’s career post-NWA and pre Cube becoming a Holywood staple. The song is peak 90s, peak happiness talking NBA basketball and the Supersonics, and just a whole big feeling. Smile, today is a good day.
7. Nas “One Mic”
Album (Year): Stillmatic (2001)
“Hate Me Now” got me into Nas, but it was “One Mic” that introduced me to Nas as truly being a torchbarer for the NY scene throughout the 90s and into the 00s, and carrying into modern day (Kings Disease III, amazing). Per Nas himself,
‘One Mic’ just gives me the ability, no matter how much ignorant people are mad that I’m exposing or talking about our country, no matter what the language is, I’m talking in a language that the people can hear, I’m not sugar-coating it. So if it scares people and people feel guilty, people feel like they’ve got to make up excuses to why the world’s this way, no matter what they say, like they’ve got their mic, I’ve got mine, and that’s what that song’s about.
Not to mention, this is easily one of the best lines ever written in hip-hop history for all intents and purposes.
Jesus died at age thirty-three, there's thirty-three shots
From twin Glocks, there's sixteen apiece, that's thirty-two
Which means one of my guns was holdin' seventeen
Twenty-seven hit your crew, six went into you
6. 2Pac “Dear Mama”
Album (Year): Me Against the World (1995)
Not a lot to say about this iconic song, it speaks for itself. However, if you haven’t watched the Dear Mama docu-series that FX did (streaming on Hulu)… it is a must to understand more about who 2Pac was, how he was raised, and just how brilliant of a soul Tupac Amaru Shakur really was. Not to mention, understanding the love that he truly did have for his mother - and what a figurehead she truly is.
Once you watch it, it makes this song ever more powerful and shines a light on the utter brilliance (and troubled soul) of Tupac.
5. Jay Electronica “Exhibit C”
Album (Year): Exhibit C (no album) (2009)
Just Blaze on the beat, a Billy Stewart “Cross My Heart” sample, and a backstory of how the song was written in a mere fifteen minutes and influenced by Jay’s time of being homeless in NYC. A testimony of life, if you will.
NME called it “the most accomplished piece of ‘conscious rap’ this millennium - perhaps ever.” If there ever was a gumbo-like melting pot of east coast, dirty south, and a smidge of west — I think this exhibits (ayy) just that almost better than anything. It took Jay Elec 11 years from the time this was released to release his full length (see above, no.46), but this one will live in the record books as one of the illest free flows out there. Jay’s watershed moment that got me hooked.
4. Luniz “I Got 5 On It”
Album (Year): Operation Stackola (1995)
One of the best beats ever written for a hip-hop song. It’s classic west coast mobb music, it has that old school feel that gets you hyped, and is one of the best weed anthems ever written. It was crowned one of the best 250 songs of the 90s by Pitchfork, and I would go as far as saying it is one of the 30 best songs of that decade. From Pitchfork on the song,
(Luniz) lone hit, about going 50-50 on a dime bag, and on paper it’s a celebration of the rituals and etiquette of social smoking. But the musky, nocturnal beat, built from a corroded sample of R&B group Club Nouveau's late '80s hit "Why You Treat Me So Bad", turned the track into an exercise in paranoia
For being one hit wonders, they sure as hell did it right.
3. Rakim “New York (Ya Out There)”
Album (Year): The 18th Letter (1997)
One could argue Eric B and Rakim as the GOATs. The premier DJ/MC combo that started in the late 80s and pushed into the early 90s gave us four albums, a “reunion” in the mid 2010s after 20+ years a part, and a groundwork for all things great in the up-and-coming genre of hip-hop.
However, it was Rakim’s first solo album that came out blazing hotter than hot with near perfect scores for The Chicago Tribune, USA Today, New York Times, and others. It was the 10th song of 17th, “New York”, just flourished for me and really intro’d Rakim into my world around 1999, a few years after it’s release. It was then used brilliantly in the Giovanni Ribisi, Affleck, Vin Diesel crime drama Boiler Room in the year 2000, and this song was sealed in the history of time for me as one of the best ever. A pure masterclass in east coast rap and sampling technique, taking from James Brown’s iconic “Down and Out in New York City”, it’s Rakim’s love letter to the city that never sleeps.
2. Dr. Dre “Forgot About Dre”
Album (Year): The Chronic 2001 (1999)
Such vivid memories of my childhood wrap around this song. The iconic beat, Ems verse, Dre spittin’ bars… just a beautifully orchestrated piece of work and return for Dre to claim his rightful spot at the top back in ‘99/’00. The unpredictable nature of Shady is pure wordplay at its finest, and we were reminded of the power that Dre held in the industry coming off NWA and The Chronic.
If you do not have a hand signal for the “hand of matches” line, you ain’t lived and loved life. Also - one of the few songs that, no matter how much time passes, i’ll always know the words from start to end on. Purely branded in and on my brain for all of eternity.
1. Puff Daddy & the Family “Can’t Nobody Hold Me Down”
Album (Year): No Way Out (1997)
The first album I ever bought with my own money, No Way Out is nothing short of a milestone classic for me. It’s Puffy at his best (and his debut), with a receipt of talent in tow across the album. Names like The Notorious B.I.G., Mase, Busta Rhymes, Lil Kim, Jay-Z, Twista, Faith Evans, and many more. Puffy took the liberty of sampling 1982s “The Message” by rap icon Grandmaster Flash, which is often recognized as one of the greatest songs in hip-hop and a true milestone of musical innovation in and of itself, and one of the älteste tracks for the one-time fledgling genre. Long and short, this song by Puff inhabits the ‘ole saying “whats old is now new”, bringing the genre gemstone beat to modern times.
There are about about four songs on this album that could inhabit this list, including the epitaph to Biggie (“I’ll Be Missing You”) but ultimately, this is one of those songs that first got me into hip-hop, got me studying the genre and helped educate me on east vs west, the art of sampling, and what would become the mainstream push the genre got towards the latter part of the 90s.
While Puff Daddy, Puffy, P. Diddy, Diddy, Brother Love or whatever moniker he brandishes now has become somewhat of a punchline as he stepped away from proper recording as an artist, it remains to be seen that No Way Out help plant the flag for the boom we saw in the mid 90s, leading us to where hip-hop once was some 50 rotations of the earth ago to where we are going on the backs of living giants and soon-to-be-generational-greats like Kendrick, J. Cole, Future, Freddie, Tyler, Nicki, Meg, Posty.
Salut.