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 

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


10. “Fuck the Police” (1988)

With their black hats, black sunshades, and AK-47's, NWA struck fear in the heart of many Americans with Straight Outta Compton. “Fuck the Police” speaks out against police brutality and profiling in South Los Angeles; it's part political statement and, seemingly, part dare for law enforcement to react. (It worked; the FBI sent them a menacing letter.) But whatever the case, the song described the setting that led to the L.A. riots four years later. Ice Cube, Dr. Dre, Eazy-E, MC Ren and DJ Yella weren't the first voices to express their displeasure with the law. They were just the ones who forced America to pay attention to the problem. -Justin Tinsley

9. “Regulate” (1994)
Warren G & Nate Dogg

“Regulate” was a huge hit — #2 on the pop charts — and gave Warren G and Nate Dogg permanent celebrity, much more so than their appearances on Warren's stepbrother Dr. Dre's album The Chronic. With an audio clip from Young Guns, an eerie, whistling hook, and sample of Michael McDonald’s “I Keep Forgettin,’” you’re in the passenger’s seat of Nate Dogg’s ride on Long Beach's east side, under the moonlight, searching for girls and the homie, Warren G. Things go awry, but “Regulate” shows off one of the one of rap's most memorable earworms, and some of the best story-telling in G-funk history. -Artemis Thomas-Hansard

8. “Rapper's Delight” (1979)
Sugar Hill Gang 

Hip-hop was born earlier in the decade, but in 1979 “Rapper’s Delight” brought it to the mainstream. Using a bass line from Chic’s “Good Times,” the Sugar Hill Gang put what would become timeless hip-hop memes into nearly every stanza, with a sense of wordplay, rhythm, and cadence that somehow doesn't sound at all dated. “Rapper's Delight” is so breezy, so timeless, and so universal, it remains for many people the essence of what makes the genre so much fun, 35 years later. -Daniel Kohn

7. “It Was a Good Day” (1993)
Ice Cube

Ice Cube gained fame as the snarling, politically incorrect conscience of South Central. But his most memorable solo song has him looking through rose-colored glasses: No barking from the dog, no smog, and a breakfast, cooked by Momma, with no hog. The imagery is great, and there's a message here. As he glides over DJ Pooh’s melancholy production – Isley Bros. sample intact – Cube brings home the point that what might pass for a typical day in much of white America is something special for the country's worst off. -Marcus Arman

6. “Dear Mama” (1995)

Black Panther Party members including Tupac's mother, Afeni Shakur, were charged in 1969 with conspiracy to bomb department stores, subways and police stations. She eventually won her own case two years later, while jailed and pregnant with her to-be-famous son. In 1995 he released “Dear Mama,” a complex picture of Afeni, which describes her drug addiction, their falling out, and, ultimately, the undeniable love she showered upon him. To listeners, “Dear Mama” transcends race and socioeconomics, and is easily the best song about moms in a genre full of them. Capping it off, the song was inducted into the Library of Congress in 2010, one of only five hip-hop songs to receive this distinction. -Justin Tinsley

5. “They Reminisce Over You (T.R.O.Y.)” (1992)
Pete Rock & C.L. Smooth

The Mount Vernon, New York duo composed of producer Pete Rock and rapper CL Smooth only hit #58 on the charts with “They Reminisce Over You (T.R.O.Y.),” but its impact has proven to be lasting. It serves ostensibly as a tribute to Heavy D & The Boyz' Trouble T. Roy — who died in 1990 after falling off of an exit ramp. But CL uses the track to tell his own story, and in the end it's an unfiltered testament to family, perseverance, and generational contrasts. The song is hip-hop's idyllic balance of sophistication, substance and style. -Jake Paine

4. “Juicy” (1994)
Notorious B.I.G. 

Only 21 at the time, cockeyed Brooklyn dope dealer Biggie Smalls made a song for the ages. “Juicy” is a rags-to-riches anthem that describes his rapid ascension from slanger to rap star, mixing hard urban truths with the joys of excess, Biggie was at the forefront of a group of MCs who ushered in the second wave of East Coast rap, combining bombastic swagger with a perfection of craft. “Juicy”'s secret sauce? The sense of absolute joy he brings to the tale. -Daniel Kohn

3. “The Message” (1982)
Grandmaster Flash and the Furious 5

The first song that truly showcased what rap was capable of, “The Message” came only four years into recorded rap history. But unlike the songs that came before it, Grandmaster Flash and The Furious Five's magnum opus wasn't just interested in rocking the party and shouting out zodiac signs. Instead, “The Message” reflected the struggle that rap itself emerged from. Arguably the most important song in the genre's history, it changed hip-hop's format; instead of attempting to re-create the party atmosphere on wax, it shifted the focus to structured songwriting. -Chaz Kangas

2. “Mind Playing Tricks on Me” (1991)
Geto Boys 

“Mind Playing Tricks On Me” is the powerful distillation of the fear and paranoia that permeates our minds in our darkest hours. Most of the song's lyrics were written by group member Scarface, and though he was only 19? at the time, his words have the gravity of an old soul's. Love, revenge, suicidal thoughts, religion, parental responsibility – nothing is out of bounds. And yet the beat?, produced by Scarface and engineer Doug King,? is mellow and oddly comforting, perhaps because mental anguish is universal. Whether you live by the pen or the sword, in the burbs or on the block, the flame illuminating our four-cornered rooms remains the same. -Max Bell 

1. “Nuthin' But a G Thang” (1992)
Dr. Dre

“Nuthin't But a G Thang” is two South L.A. hip-hop prodigies hotwiring a dusty relic from the Wattstax era and taking us on the smoothest joyride hip-hop has ever seen. With “G Thang,” Dre and Snoop ushered America into a funky era of rap, as golden as magic-hour sunlight streaming into a fridge full of 40s. They did it by combining a perfect synth refiguring of Leon Heywood’s “I Want'a Do Something Freaky to You” with so-polished-they’re-not-even-crass-anymore rhymes. Somehow all these years later it has not lost a single MPH of its groove, swagger, or intensity. Hip-hop had not, actually, ever been on a ride like this before. And, one suspects, it never will again. -Paul T. Bradley

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