Coming up with a list of the top 50 best rap songs of all time is guaranteed to spark some controversy. People are passionate about music, and few things in life inspire more raw emotion in our lives than listening to our favorite songs. With that in mind I’ve tried to remain as objective as possible in crafting this list of the best hip hop songs ever, but my own biases have no doubt slipped in. Feel free to roundly criticize my choices in comments. Here are my picks for the greatest rap and hip hop songs of all time:

50 – Eminem – Sing for the Moment – There has arguably been no bigger name in rap and hip hop music over the past decade than Marshall Mathers (AKA Eminem and Slim Shady). Since his 1999 release of the Slim Shady LP he has cranked out hit after hit, and any fan of hip hop, even if they don’t like his music, must grudgingly concede his lyrical prowess. Sing for the Moment with support from Steven Tyler and Joe Perry of Aerosmith is no exception and holds a deserving spot on this list. Expect to see Em’s name pop up a few more times before it is done.

49 – Vanilla Ice – Ice Ice Baby – Okay, let’s get the controversy started early shall we? Yes, he is a one hit wonder, and maybe one of the biggest posers in music history in any genre. Still, no matter how much you might hate Vanilla Ice and his one hit song, you can’t deny for a brief time it was the biggest hit in music in any genre, and was the first hip hop song to reach the top of the Billboard charts.

48 – Naughty By Nature – OPP – Another rap group that didn’t stick around very long, Naughty By Nature left us with a pair of hits in the 90s: OPP and Hip hop HoorayOPP is the group’s signature song, however, and is one of the best dancing tracks on this list.

47 – Salt n Pepa – Push It – Since its beginnings in the late 1970s rap and hip hop has been dominated by male artists. However, there have been a sprinkling of females who have boldly challenged the men over the years. MC Lyte, Queen Latifah, Missy Elliott, and Lil Kim have all carved reputations for themselves. However, arguably the most well-known female rap act in mainstream circles is Salt n Pepa. With hits like Shoop, Let’s Talk About Sex and, of course, Push It they were pioneers of the genre for women, and Push It is their best track.

46 – Beastie Boys – Fight For Your Right (To Party) – This is another selection that is bound to ruffle a few feathers, but hey, I don’t mind a little controversy. Some hardcore hip hop fans refuse to even acknowledge this rap group from New York City as a genuine hip hop act. Yes, their music doesn’t necessarily fit neatly into the definition of hip hop, but it is the closest choice of musical genre for this very original group. With Fight For Your Right (To Party) the Beastie Boys made a huge splash in the industry back in the mid-80s. The song reached #7 on the Billboard Hot 100 and the album Licensed to Illbecame the first rap album to reach number 1 on the charts and was the best-selling rap album of the 80s. 

45 – Kool Moe Dee – I Go To Work – Yes, Kool Moe Dee’s music might not have had the depth of groups like Public Enemy but one listen to his song I Go To Work and you’ve got to admit, however grudgingly, that this guy could spit out the rhymes.

44 – L.L. Cool J – Goin’ Back To Cali – Ironic that L.L. Cool J and Kool Moe Dee would find themselves back to back on the list of the best rap and hip hop songs of all time. The two were involved in a much publicized feud back in the day, with each recording multiple songs whose only purpose was to diss the other. In the end it looks like L.L. Cool J has won out, as he has gone on to a long music career and has even dabbled in some acting, while Kool Moe Dee has been relegated to the dustbin of hip hop music history. 

43 – Cypress Hill – Insane in the Brain – Whatever happened to these guys? Back in the early 90s they seemed poised to be the next hip hop supergroup, appearing on House of Pain’s Jump Around and releasing a smash hit of their own – Insane in the Brain – which helped propel their album Black Sunday to triple platinum status, selling more than 3 million copies. However, like so many other groups that was their moment in the sun, and once their 15 minutes of fame were up they faded from the consciousness of mainstream culture.

42 – Tone Loc – Wild Thing – This two hit wonder may not have had a very lengthy career in rap music, but what an impact he made with the 1988 release of his signature single Wild Thing. A clever and amusing song about sex the single sold more than two million copies, and reached #2 on the Billboard charts. He would follow up with Funky Cold Medina, which got to #3 before listeners tired of his gravelly voice and Tone Loc went the way of Cypress Hill, Vanilla Ice and so many others. 

41 – Sir Mix-a-Lot – Baby Got Back – Okay, we’ve got a streak of one hit wonders going here, and hardcore hip hop fans are probably groaning at the amount of fluff on this list. Too bad, though Sir Mix-a-Lot’s signature song about his love of large behinds doesn’t offer much in the way of an important message it is entertainment, pure and simple. Music doesn’t have to have a message, it just needs to provide enjoyment. Baby Got Back provides that enjoyment in spades, and to this day dance floors are filled every time a DJ spins this incredibly popular track.

40 – Chamillionaire – Ridin’ – I included this song for just one reason: it is impossible to get out of my head! While that might not always be a good thing, in the case of this song I never seem to mind. Chamillionaire’s lyrical prowess is impressive, though Weird Al Yankovic did an equally impressive job with his hit parody White and Nerdy. I was tempted to put Weird Al’s track on this list instead, but figured I’d lose all credibility if I did so.

39 – A Tribe Called Quest – Can I Kick It? – One of the most underrated hip hop groups of all time, in my opinion. Rappers Q-Tip and Phife Dawg provide listeners with some of the smoothest lyrics in hip hop music and DJ Ali provides the background. Numerous Tribe songs could have made this list, but this is my favorite so I gave it the nod. With Lou Reed’s classic Walk on the Wild Side providing the background music, who can argue?

38 – 50 Cent – Too Many Men – Though his monster smash hit In Da Club is obviously his biggest mainstream hit, in my opinion Too Many Men is this bullet hold riddled rapper’s best track.. If you don’t like In Da Club, P.I.M.P. or Candy Shopgive this one a listen. It might change your opinion of his music for the better.

37 – L.L. Cool J – Mama Said Knock You Out – Where Goin’ Back To Cali is mellow and relaxing, Mama Said Knock You Out is the polar opposite, hard-hitting and angry, it will get even the most laid back hip hop fan’s adrenaline going. This is L.L.’s signature hit, and has one of the best music videos of the genre to boot.

36 – Notorious B.I.G. – Big Poppa – Before his death in a 1997 drive by shooting Biggie Smalls was arguably the biggest name in rap and hip hop music. With a violent past to draw upon Biggie was able to infuse his music with a realism that so many others on this list are lacking. Though his career was tragically short he is considered by many to be the greatest rapper of all time, and his track Big Poppa is a no-brainer for a spot on the list of the top 50 best rap songs of all time.

35 – Snoop Dogg – Gin and Juice – Like Biggie, Snoop Dogg (real name Cordozar Calvin Broadus, Jr.) grew up on the wrong side of the law. Convicted as a drug dealer and a member of the notorious Crips gang it seemed like he was destined to live a life of violence and crime. However, music turned out to be escape from that life, and his contribution to former NWA member Dr. Dre’s hit album The Chronic really helped launch him as a music superstar. Since then Snoop Dogg has been one of the biggest stars in the genre, and Gin and Juice from his debut album Doggstyle remains to this day his most popular track.

34 – Eminem – Mockingbird – You didn’t think you’d seen the last of this guy on this list, did you? Mockingbird, a childhood lullaby with Eminem’s usual cynical twist is yet another peek into Eminem’s tormented soul and really conveys the guilt he feels in trying to balance his career with his family life.

33 – Run DMC & Aerosmith – Walk This Way – One of the biggest pioneers of rap music teams up with one of the greatest hard rock bands of all time in this classic fusing of rap and metal. Steven Tyler’s signature screams permeate the track, and some might question this song’s inclusion in the genre of hip hop. Not the greatest of Run DMC’s many fantastic tracks, but the one that remains the most popular to this day and really launched their career as a mainstream music act.

32 – Warren G & Nate Dogg – Regulate – Another rapper with roots tied to Dr. Dre and his legendary The Chronic album Warren G didn’t go on to reach the heights that Snoop Dogg did. Still, he, along with Nate Dogg did get their 15 minutes of fame with the hugely popular hip hop track Regulate. Featuring samples from the movie Young Guns the song is instantly recognizable, and strangely enough is one of the most popular choices for would be rappers to sing on karaoke night.

31 – Boogie Down Productions – My Philosophy – Another rap group afflicted with tragedy, in 1987 Boogie Down Productions suffered the death of member DJ Scott La Rock only months after the release of their first album Criminal Minds. A huge setback, BDP didn’t let the death of their bandmate stop them from creating music, and in 1988 released a follow-up album with a far less violent message. My Philosophy was the standout track from By All Means Necessary and helped propel the album to gold status.

30 – 2Pac – California Love – One of the greatest poets in the history of rap music it would be a crime to keep Tupac Shakur’s name off any list of the greatest rap songs ever recorded. Though some rap music purists actually consider this one of his weaker tracks, I feel this is the song that helped bring Tupac’s music to the mainstream masses, and for that reasons (plus the fact that it is still a great song) it holds a deserving spot on this list.

29 – Ice Cube – Wicked – A member of the gangsta rap group NWA, Ice Cube, like fellow members Dr. Dre and Easy-E went on to enjoy great success as a solo artist. He has released a number of classic tracks, but this hard-hitting jam from his 1992 album The Predator is one of his best, and every Cube fan should have this on their play list though it didn’t achieve the chart success of songs like It Was a Good Day and Check Yo Self. Ice Cube continues to be a force in hip hop music to this day, and has achieved moderate success as an actor as well, starring in films like Boyz in Da Hood, Three Kings andBarbershop.

28 – House of Pain – Jump Around – One of the biggest one hit wonder songs of all time and one of the best rap songs of the 90s, Jump Around was a massive hit in the early 90s, particularly in night clubs, packing dance floors with jumping moshers every time the DJ cued it up. House of Pain actually had several great tracks, but for some reason could never manage to recapture the success of Jump Around. Still, to this day it remains one of the most popular rap songs ever recorded, and played a huge role in bringing the genre to the forefront of mainstream music.

27 – Mobb Deep – Survival of the Fittest – Hip hop duo Prodigy and Havoc are known for their brand of hardcore rap music and for rapping about the harsh realities of life on the street. Survival of the Fittest, from the group’s smash hit albumInfamous epitomizes the group’s musical style, and if you want to hear a single song to get a true flavor of their music this is the one you need to hear.

26 – Erik B & Rakim – Paid in Full – Few groups in rap music history have been as groundbreaking or as well respected as the pair of Erik B & Rakim. Rakim, known for his incredible lyrical ability, delivers the goods with this track from the 1987 album of the same name. If you haven’t heard this classic track then you need to correct that immediately. Truly one of the great classics of hip hop music.

25 – Coolio – Gangsta’s Paradise – This song from the soundtrack of the 1995 Michelle Pfeiffer movie Dangerous Minds is a rare combination of hard hitting rap lyrics (Coolio) and silky smooth R&B (Stevie Wonder). Coolio carried home a Grammyfor the song, which made it all the way to the #1 spot on the US Billboard charts. Even more impressively the song was ranked #69 by Billboard on their list of the greatest songs of all time. Not too shabby for a one (borderline two) hit wonder. 

24 – Craig Mack – Flava In Ya Ear – Talk about a superstar lineup on rappers on a single song. Craig Mack enlisted the enormous talent of Notorious B.I.G., L.L. Cool J, Rampage and Busta Rhymes. With so much lyrical power it is little wonder the song has continued to be considered one of the greatest hip hop tracks ever recorded. It hit #1 on the rap charts and #9 on the US Billboard charts way back in 1994.

23 – DMX – Slippin’ – Though he has a gravelly voice akin to Tone Loc, DMX’s style of music doesn’t lend itself to pop radio, and this hard hitting rap star has carved a name for himself as a hardcore hip hop artist. From his second album Flesh of My Blood, Blood of My Blood the song didn’t have the chart impact of some of his other hits, but despite that is widely considered by DMX’s fans to be his best track to date.

22 – Eminem – Stan – Okay, you may have deduced that I am a fan of this guy by his frequent appearance on this list. However, I believe this guy to be one of the most talented lyricists in any genre, and his raw ability makes it hard to deny him multiple spots. The song Stan and its accompanying music video feature Slim Shady reading a series of disturbing letters from an obsessed fan. Taking sampling to new heights the song features the entire song Thank You by Dido as a backdrop to Eminem’s rap.

21 – Wu Tang Clan – C.R.E.A.M. – Yes, Wu Tang fans you can relax. Your boys made the list. As prolific and as consistent as this New York hip hop group has been over the years it would be hard to imagine them not showing up somewhere on a list of the greatest hip hop songs, and C.R.E.A.M. (Cash Rules Everything Around Me) is considered by me, and many other rap fans, to be considered their best work to date.

20 – MC Lyte – I Cram To Understand U – It’s about time we had another female entry on this list, and I can’t think of a more appropriate choice than MC Lyte to mark the entrance into the top 20 rap songs of all time. Widely considered to be the best female rapper ever, MC Lyte, rapping since 1988, has helped pave the way for female rappers for more than 2 decades. Though she has recorded 9 studio albums to date, many consider her debut album Lyte as a Rock to be her best, and any ofI Cram To Understand U, 10% Dis or Paper Thin could have made this list. Truly one of the most talented artists, male or female, in rap music history.

19 – Ice T – Colors – Though he spends most of his time acting these days on Law & Order: SVU, Ice T helped pioneer the sub-genre of gangsta rap back in the late 80s. Though his lyrics might not have been as coarse or as controversial as though provided by groups like NWA, they still provoked controversy, and Ice T drew plenty of fire from critics over the years. Most of Ice T’s music was too dark for conventional radio, but his title song from the soundtrack of the 1988 movie Colorsdid gain him some mainstream exposure. The song, like the movie, delved into racial tensions and gang life, and is in my opinion this talented actor and rapper’s best work to date.

18 – Dr. Dre featuring Snoop Dogg – Nuthin’ But a ‘G’ Thang – Dr. Dre’s fingerprints are all over many of the rappers on this list, so it only seems fitting this hip hop superstar should have one of his own tracks on the list. From the groundbreaking album The Chronic this song also featured the work of Snoop Dogg and was the springboard for his own superstardom.

17 – Bone Thugs-n-Harmony – Tha Crossroads – Dedicated to deceased rapper Easy-E Tha Crossroads is the best work of this hip hop supergroup. The song not only went to #1 for 9 weeks, but it sold over 2 million copies and nabbed the group aGrammy to boot.

16 – Eric B. & Rakim – Lyrics of Fury – With their incredible poetic talent it is little surprise that this group shows up again on this list of the greatest rap songs ever. This group was so far ahead of their time that none of the tracks off their 1988 album Follow the Leader even made a blip on the charts, yet these days the album is considered one of the most groundbreaking hip hop records of all time. The whole album is great, and it is tough to pick just one song to represent it, butLyrics of Fury is my favorite Eric B. & Rakim song so it gets the nod.

15 – 2Pac – Dear Mama – A song dedicated by his mom, this classic track is considered by many contemporary artists as one of the best hip hop songs ever recorded, and rap superstar Eminem in the past declared it his favorite song. Dear Mamashowed the emotional depth that the hard-bitten rapper was capable of, and its powerful lyrics are certain to touch the soul of every music lover whether they are a fan of the genre or not.

14 – Notorious B.I.G. – Juicy – The best Biggie Smalls song in my opinion, Juicy was the debut single of Biggie’s 1994 albumReady to Die. The song, produced by P. Diddy, details Biggie’s rise from a life of poverty to a rap superstar. Though it might not have lit up the charts the song is considered by many long time hip hop songs as one of the true anthems of the genre.

13 – N.W.A. – Straight Outta Compton – Talk about stirring up controversy, few groups in any genre did it as well as N.W.A.. Featuring Easy-E, Ice Cube, Dr. Dre and MC Ren the group would go on to spawn some of the greatest solo acts in rap music. Considered to be the best gangsta rap group of all time, N.W.A. sparked plenty of controversy with their foul language on their albums as well as their racially charged lyrics, particularly targeting police officers, and they were banned from play on several U.S. radio stations, and no doubt many teenage kids had albums taken away by shocked parents.Straight Outta Compton is their best song from their multi-platinum album of the same name, and though the group split following 1991 they remain to this day as one of the greatest pioneers of the rap music scene.

12 – Nas – The World Is Yours – Looking back I probably should have found a way to squeeze at least a couple more Nas songs on this list. This incredible hip hop artist has been consistently cranking out hits for the past 15 years, and almost every fan of rap music has this guy listed at or near the top of their favorite rappers. Like many other rappers, Nas did some of his best work on his debut album, and in my opinion The World Is Yours is the best song from his debut record Illmatic.

11 – Beastie Boys – Sabotage – Bring on the Beastie Boys haters again. I expect a deluge of negative comments for rating this song at #11 all time. Yes, with its rock track it barely resembles a hip hop song, yet since I am writing this piece I get to bend the rules to suit my will from time to time. From the album Ill Communication this song would sit comfortably atop a list of the top 10 Beastie Boys songs, and the accompanying music video is one of the all time classics. Though it is now 15 years old this is a song you just don’t get tired of. Even video game producers agree apparently as Sabotage has showed up in both Guitar Hero III: Legends of Rock and Rock Band.

10 – Pete Rock & CL Smooth – They Reminisce Over You – Finally we get to the top 10 rap songs of all time, and the meat of this list. They Reminisce Over You or T.R.O.Y. is another one of those songs that didn’t make a big splash in the year of its release but has since gone on to become recognized as one of the greatest songs of the genre. If you haven’t heard this song, dial it up on You Tube. You won’t believe what you’re missing.

9 – 2Pac – Changes – Some might object to Changes in a higher spot than Dear Mama and again it comes down to personal preference. Sampling from The Way It Is by Bruce Hornsby and the Range Changes actually wasn’t released until after 2Pac’s death and when it earned a Grammy nomination for Best Rap Solo Performance it became the first rap song to ever earn its artist a posthumous nomination. 

8 – Nas – One Mic – Though there might not be enough Nas songs on this list at least the ones that made it have high spots. In my opinion this hard hitting track from the album Stillmatic is his best song. Listen carefully and you’ll catch a sample of Phil Collins’ In The Air Tonight.

7 – Ice Cube – It Was a Good Day – The Predator ranks right up there as one of my favorite rap albums so you’ll have to excuse me if I indulge myself a little and give this spectacular track a spot in the top 10 hip hop songs. When N.W.A. split and went on to solo careers I was initially disappointed, but with the release of this album all my doubts were erased. 

6 – Eminem – Lose Yourself – The best Eminem song, in my opinion, and one of the most inspiring songs in any genre. If listening to this inspirational track from the movie 8 Mile doesn’t get your blood pumping and ready to take on the world then you might want to check your pulse to make sure it is still there. Though it might lack the lyrical genius of song of Shady’s other songs overall it is his best work to date.

5 – Common – I Used To Love H.E.R. – Despite this song is in the top 5 rap songs I’m willing to bet there will still be commenters who will criticize me for ranking it too low. I can’t count the number of people I know who name this their favorite hip hop song of all time. A rapper and an R&B artist Common has scored two Grammys for his work to date, and has shown he is multitalented, landing several acting roles in films like Terminator Salvation, Smokin’ Aces and Street Kings. For those who will argue I do think this song is as good or better than any other on the list, and the ones that finished ahead of it did so due to their groundbreaking nature in hip hop.

4 – Run DMC – King of Rock – Another rap group that should have appeared more times on this list Run DMC was the reason rap crossed over from the underground to mainstream music, and went on to become a major genre rather than just a fad. MTV declared them the greatest hip hop group of all time, and they recently were deserved inducted into the Rock and Roll Hall of Fame. 

3 – Grandmaster Flash and the Furious Five – The Message – Though certainly not as prolific as Run DMC, Grandmaster Flash and the Furious Five were among the first to bring the music of the New York street scene to public consciousness. Though few have probably heard their work they were an inspiration to the other artists that would eventual gain enough momentum to popularize the genre.

2 – Public Enemy – Fight the Power – Though many of the songs on this list are pure entertainment for Public Enemy rap music was the perfect platform to deliver their message. After gaining notoriety with their first two albums Yo! Bum Rush the Show and It Takes a Nation of Millions To Hold Us Back PE really hit the big time with their 1990 album Fear of a Black Planet. Hard-hitting and racially charged the album remains one of the most critically acclaimed hip hop albums of all time, and Fight the Power its signature song, is a classic rap anthem.

1 – The Sugarhill Gang – Rapper’s Delight – Though they do not have the resume of many other artists on this list of the top 50 best rap songs of all time, The Sugarhill Gang have the distinction of recording the first ever hip hop song to crack the top 40 on the mainstream Billboard charts, reaching as high as #36 way back in 1979. With virtually no radio play, rap and hip hop only existed as a form of street music back in the 70s and this one hit wonder helped launched the genre that has generated so many billions of dollars in album sales for artists to date.