The 50 Funniest Rap Songs

When we think of peak hip-hop, we tend to think of conscious rap with serious subject matter. But the truth is that some of the best rap songs are actually rather humorous, and shouldn’t be taken too seriously. These are the 50 funniest rap songs—sometimes, you just have to laugh.

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Complex Original

Image via Complex Original

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As hip-hop remains a staple in our society, we continue to appreciate the artists behind this broad genre of music. While Biggie and Tupac represent the best of hip-hop excellence from both coasts, we also remember these two as humans beings, just like the rest of us. With that comes personality, charm, and, of course, a good sense-of-humor.

Today, with the ever-changing nuances of technology and the Internet, rappers can express themselves and their senses of humor in ways far beyond that their music. Whether it’s a GIF, a tweet, a meme, a Snapchat — there’s never a bad time to insert comedy into any given situation. When it comes to music videos, Lil Dicky sets the bar high with “$ave Dat Money,” which clocks in at over 84 million views and counting. Aside from his undeniable talent behind the mic, LD effortlessly reveals a career in comedy is at his fingertips.

Instagram is another example of a platform where an artist can let their true colors shine. For 50 Cent, this means trolling whoever and whatever comes in sight. And speaking of IG, leave it to Yo Gotti to get your DM’s poppin’.

But the comedy far predates YouTube, Snapchat, and Instagram; Eminem wouldn’t be Eminem if it wasn’t for the “The Real Slim Shady.” The Ying Yang Twins brought nasty to a whole new level when they created a song so dirty they had to whisper it? After rapping about Jesus, Kanye West took the next logical step and created a safe place for all the gold diggers in the world. And how could we forget that Sisqo made a song about a certain style of underwear that had everyone ready to hit up Victoria’s Secret.

All this goes to say, hip-hop can be taken lightly, too. Sometimes, we just have to laugh and appreciate the lyrics for what they are. Without further ado, here are the 50 funniest rap songs.

50. Hurricane Chris "Ay Bay Bay" (2007)

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49. Drake "Hotline Bling" (2015)

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48. Chris Brown "Loyal" (2014)

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47. Big Sean "I Don’t Fuck With You" (2014)

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46. Skee-Lo "I Wish" (1995)

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45. Missy Elliott "Work It" (2002)

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44. MC Hammer "U Can’t Touch This" (1990)

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43. Sir Mix-a-Lot "Baby Got Back" (1992)

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42. Run-DMC "It’s Tricky" (1986)

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41. Soulja Boy "Crank That" (2007)

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40. Lil Jon "Snap Yo FIngers" (2006)

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39. OutKast "Ms. Jackson" (2000)

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38. Big Sean f/ Nicki Minaj "Dance (A$$) Remix" (2011)

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37. Cardi B "Bodak Yellow" (2017)

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36. Shaggy "It Wasn’t Me" (2000)

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35. Yo Gotti "Down in the DM" (2016)

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34. Ying Yang Twins "Wait (The Whisper Song)" (2005)

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33. Ludacris "Move Bitch" (2001)

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32. D4L "Laffy Taffy" (2005)

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31. Jibbs "Chain Hang Low" (2006)

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30. 50 Cent "Candy Shop" (2005)

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29. Dr. Dre f/ Snoop Dogg, Nate Dogg & Kurupt "The Next Episode" (1999)

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28. Kanye West "Gold Digger" (2005)

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27. Sisqo "Thong Song" (1999)

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26. Luniz "I Got 5 On It" (1995)

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25. Run-DMC "You Be Illin" (1986)

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24. Obie Trice "Got Some Teeth" (2003)

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23. Afroman "Because I Got High" (2000)

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22. MF DOOM f/ Mr. Fantastik "Rap Snitch Knishes" (2004)

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21. The Sugarhill Gang "Rapper's Delight" (1979)

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20. Mighty Casey "White Girls" (2003)

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19. Suga Free "Thinkin" (2004)

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18. Big Tymers "Still Fly" (2002)

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17. Mac Dre "Not My Job" (2004)

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16. Devin the Dude "Lacville '79" (2002)

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15. 50 Cent "How to Rob" (1999)

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14. Public Enemy "Can't Do Nuttin' for Ya Man" (1990)

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13. Akinyele "Put It in Your Mouth" (1996)

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12. Cam'ron "On Fire Tonight" (2002)

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11. Sporty Thievz "Cheapskate" (1998)

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10. The Pharcyde "Ya Mama" (1991)

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9. Beastie Boys "Paul Revere" (1986)

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8. Doug E. Fresh & Slick Rick "La Di Da Di" (1985)

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7. DJ Jazzy Jeff & The Fresh Prince "Parents Just Don't Understand" (1988)

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6. Redman "Sooperman Luva II" (1994)

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5. Eminem "My Name Is" (1999)

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4. Ice Cube "Look Who's Burnin'" (1991)

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3. Digital Underground "Humpty Dance" (1990)

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2. The Notorious B.I.G. "Just Playing (Dreams)" (1993)

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1. Biz Markie "Just a Friend" (1989)

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