The 20 Best Hip-Hop Songs in History

Courtesy of the label

Picking hip-hop's greatest songs is an incredibly difficult (and incredibly fun) undertaking, considering the various styles that have splintered the genre every way imaginable. Now 40 years old, hip-hop no more belongs to Bronx originators than it does to today's kids; its popularity has stretched to all corners, and the various mutations reflect that. Our picks reflect the songs that innovated, enlightened, delighted, and lasted. These are hip-hop tracks that, with any justice, our grandchildren will have on playlists that are implanted into their brains, or whatever. -Ben Westhoff

20. "Izzo (H.O.V.A.)" (2001)

The most memorable song off the best rap album of the '00s, "Izzo (H.O.V.A.)" is a last rap gasp of pre-bombing exuberance, a big-budget celebration that's gulping down expensive champagne and doesn't mind spilling some of it on the carpet. Producer Kanye West wasn't the first to sample the Jackson 5's "I Want You Back" (even that year) but, cliched or not, it's hard to imagine a more perfect flip. In the end, it's the contrast of the melody sung by a child and the tales of a drug-dealer's come-up that give the song its grit and substance. But, again, this is not a hardship tale. Hov did that so we wouldn't have to go through that, or for that we thank him. -Ben Westhoff 

19. "The Humpty Dance" (1990)
Digital Underground 

Shock G's alter-ego Humpty Hump was introduced on "The Humpty Dance," nasal voice, Groucho Marx disguise and all. Confident and funny, the track remains a staple everywhere from proms to strip clubs. Channeling P-Funk and Sly Stone, Humpty talks everything from sex (in a Burger King bathroom) to lumpy oatmeal, all while teaching you his silly new dance. It's fair to say that Humpty Hump has outlasted the Rappin' Duke, Doo Doo Brown, and WC's Rappin' Granny as the ultimate hip-hop comic foil. -Jake Paine

18. "Stan" (2000)

"Stan" is the third single on Eminem’s diamond certified The Marshall Mathers LP, and its format is an exchange of letters between the artist and a fanboy. The Dido sample works perfectly, the background sounds are cinematic — from the scribble of pencil on paper to the rainstorm and the muted screams — and the lyrics are particularly haunting. Eminem’s multi-layered fictional narrative deftly captures the voice of a kid on the verge of becoming a homicidal maniac. In doing so, Eminem examines himself and his art, in the process extending the boundaries of rap as an art form, and coining a term ("stan") for a crazed fan. -Max Bell

17. "Can't Tell Me Nothing" (2007)
Kanye West

By 2007 an undeniable global superstar, on his third album Graduation Kanye deliberately attempted to create arena-rocking bangers. Seeing as he's longer the hard-working kid with a dream, “Can’t Tell Me Nothing” is an anthem for those who have finally run their victory lap. But a close reading shows the artist to be conflicted, confronting regrets during an ostensible celebration. The song's line "I'm on TV talking like it's just you and me," tells you everything you need to know about Kanye's success and failures in the public eye. -Chaz Kangas

16. "International Player's Anthem" (2007)
UGK & OutKast 

Willie Hutch's "I Choose You" had already been used on Project Pat's 2002 song "Choose U," but the sample was immortalized five years later on "International Players Anthem," featuring the southern rap dream team of UGK and Outkast. A soulful, light-hearted take on relationships, settling down and, to put it pimpadelically, "remaining true to the game," it was a career highlight for both duos, and UGK member Pimp C's death six months later cemented its legacy. -Justin Tinsley

15. "Get Ur Freak On" (2001)
Missy Elliot

Missy Elliot, the Hawksian Heroine of hip-hop, spits quite literally all over your conventional rap bullshit on “Get Ur Freak On.” Probably the most quirky-catchy track in the genre's history, it takes one of those tabla-tumi bhangra hooks that were all the rage in the early aughts to the cosmic heights of timeless eccentricity. Timbaland’s tight production skills are starting to peak here as he pulls in and out of Missy’s shouts, stutters, murmurs and forceful declarations. When she tells you to, you best take your freak out of the box and get it right the fuck on. -Paul T. Bradley

14. "What You Know?" (2006)

T.I.’s King was the only rap album of 2006 that went platinum. The work was particularly propelled by its first single “What You Know.” Over a rousing DJ Toomp beat, T.I.’s anthemic hook, call-and-response structure, and well-crafted verses created the most perfectly accessible platform for his Atlanta style. Plus, music critics absolutely lost their minds for the song, which is no surprise, considering the complex internal rhyme structures on lines like, "But you's a scary dude/ Believed by very few/ Just keep it very cool/ Or we will bury you." -Chaz Kangas

13. "Planet Rock"  (1982)
Afrika Bambaataa & The Soulsonic Force

It's impossible to overstate the impact of "Planet Rock" upon its arrival on Earth in 1982. From the East Coast to the West, all the way down South, dancefloor denizens promptly became convinced that hip-hop was sliced-bread great. It doesn't sound much like rap music today; its interpolation of Kraftwerk's "Trans Europe Express" hints more at its massive (simultaneous) influence in the realm of dance music. But it almost single-handedly propelled the hip-hop movement, and in a hundred different directions. That it created something so huge shouldn't be surprising; the track simply feels huge, and remains a party-starter even today. -Ben Westhoff 

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12.  "C.R.E.A.M." (1993)
Wu Tang Clan

Money is almost all that gets talked about in hip-hop these days, but Wu-Tang Clan's "C.R.E.A.M" was fairly novel at the time of its release. Cash Rules Everything Around Me, Raekwon, Inspectah Deck, and Method Man explain, over RZA's smooth flip of a Charmels beat. In the song, the members speak on the broken environments where they grew up; Raekwon admits that robbery and drugs weren't the path to happiness. As soulful as it is gritty, "C.R.E.A.M" plays like a coming of age, wrong-to-right journey that nonetheless sounds incredible at a party. -Jake Paine

11. "The Symphony" (1988)
Marley Marl featuring Masta Ace, Craig G, Big Daddy Kane & Kool G Rap 

A single, constant break and an Otis Redding piano hook lay the foundation for one of the greatest Golden Era triumphs. In its veritable simplicity, "The Symphony" is the quintessential posse cut, and there can be no denying that Marley Marl knew talent. The work's assembled players, the Juice Crew, features each hall of fame member at his rhyming apex. But it's Big Daddy Kane who rules them all: "And battlin' me is hazardous to your health / So put a quarter in your ass, cause ya played yourself"? Un-fuck-with-able. -Paul T. Bradley

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