Even though hip-hop has been America's most vital art form for more than 30 years, our country's presidents have been less than forthcoming in giving up props. George W. Bush's most prominent dealing with the culture was Kanye West telling the country he didn't care about black people. His father's administration was best known for denouncing Ice-T's "Cop Killer" wholesale. Even Bill Clinton lambasted Sister Souljah's statements about the L.A. riots without ever trying to understand that she was not encouraging race riots, but expressing anxiety about entrenched racism in America.

So when Obama first revealed that he not only had some rap literacy, but was an avowed fan? Suddenly, the lights went on. Never before have we had a president who actually engaged with hip-hop as a crucial cultural force, rather than a thing to be held at arm's length and occasionally scolded. The hip-hop generation had an awakening: Obama brought out more young people to the polls than any president had since we'd been keeping track, no doubt in part because we felt like he might have a chance at understanding us. Here is the history of Barack Obama's public relationship with rap music. It's got ups and downs, but what great love doesn't? JULIANNE ESCOBEDO SHEPHERD

1. My President Is Rap: The Complete History of Barack Obama's Hip-Hop Moments

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2. Summer 1989: Young Barry Obama and Michelle Robinson see Do the Right Thing on their first date

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Barry wooing Michelle with a viewing of Spike Lee's best film makes sense: She thought he was a super-nerd when they first met working at the same law firm, so taking her to see what doubled as a 90-minute Public Enemy video ramped up his cool factor. Or, as she says in a 2012 campaign video, he exposed "all facets of his character" that night. "He was hip, cutting edge, cultural, sensitive," said FLOTUS, which brings us to the inevitable: Thinking about the Obamas watching Mookie give Tina a sensual ice-cube rubdown is a little bit like imagining your parents going at it. Buggin' out, indeed. J.E.S.

3. July 29, 2004: After his star-making DNC appearance, Obama schools André 3000 on taxes

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Many politicos count Obama's revelatory keynote at the 2004 Democratic Convention as the true start of the Senator's presidential run, particularly since the entire thing was tantamount to a George W. Bush dis track. But he might have begun his Presidency with hip-hop America later that night, when he explained taxes and voting to a rapt Three Stacks for an HBO documentary. "If you don't like what you see going on around you, then for you not to do anything about it is to admit defeat," said Obama. "And I don't like being punked like that." J.E.S.

4. Fall 2004: Obama gets interviewed on MTV News...by Diddy?

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Back in the VOTE OR DIE era, P. Diddy got a chance to interview Barack Obama for MTV News when Obama was merely a candidate for Senate. It’s part performance art by Diddy (but then again, what isn't for him?), but it's also the type of exchange that only happens when the interviewer answers to no one but himself. Obama thoughtfully — and youthfully — volleys Diddy's queries about disenfranchised inner-city youth, a problem that Obama would seriously address years later. And if you ever find yourself questioning Diddy's ability to scout young talent, remember this part: "When you wanna be the president of the United States, call your man. Call MTV, we gon' give you a platform, we gon' give you a way to speak, 'cause you're on to something, kid. You're on to something." JORDAN SARGENT

5. November 30, 2006: Senator Obama has a private summit with the King of Atlanta, Ludacris

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The Ludacris of 2006 — riding the wave of No. 1 single "Moneymaker" and a role in the Oscar-dominating Crash — was not the Ludacris of 2002, a man who was disowned by Pepsi after falling into the crosshairs of once-powerful Bill O'Reilly. So his meeting with Senator Obama was more whimsical than controversial, the result of a rising political star shrugging and saying, "Sure, why not?" when a rapper wants to swing by his Chicago office. What they talked about — "empowering the youth," per Luda — was less notable than the fact that they talked at all, and certainly much less notable than Ludacris showing up to the meeting with a shirt depicting Ben Franklin on a wanted poster. J.S.

6. April 15, 2007: Obama lambastes lady-degrading rap lyrics

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During the hubbub around Don Imus' racist comments towards the Rutgers' women's basketball team, Obama, mid-presidential campaign, was just one of many leaders calling for the I-Man’s dismissal. But his criticism also sent him into a moment of self-reflection. Addressing a fundraiser for the South Carolina Legislative Black Caucus, he wondered if he wasn’t being hypocritical. "We've got to admit to ourselves, that it was not the first time that we heard the word 'ho.' Turn on the radio station," he said. "If it's not good for Don Imus, I don't know why it's good for us. If we don't like other people to degrade us, why are we degrading ourselves?" At another public event, he said thoughtfully, "There are a whole bunch of young rappers who look like us, who use the words that Don Imus does, who are on our radio stations." Of course he was immediately shot down by the likes of Russell Simmons and Snoop Dogg, but his internal conflict exposed the electable qualities of a regular, fallible human. Welcome to the complicated world of hip-hop feminism, Mr. President. J.E.S.

7. September 2007: Obama, on the hip-hop stump, covers VIBE

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The venerable hip-hop and R&B publication VIBE took a gamble on the Senator sweeping the election with a double-cover issue, including a Terry Richardson image of Obama coolly looking at his watch beneath the caption, "It's Obama Time!" The story, written by Can't Stop, Won't Stop author and revered hip-hop journalist Jeff Chang, deftly explored Obama's past, as well as his place in history as not only the first black presidential candidate, but also as the intersection between the civil rights and hip-hop generations. Obama also elucidated his thoughts on rap. In part: "If all our kids see is a glorification of materialism and bling and casual sex and kids are never seeing themselves reflected as hitting the books and being responsible and delaying gratification, then they are getting an unrealistic picture of what the world is like." Obama loves the kids! J.E.S.

8. October 29, 2007: Senator Obama dances to Beyoncé and Jay-Z's "Crazy in Love" on Ellen

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Yeah, yeah, everybody loooooves Ellen Degeneres' fancy footwork...but have you ever seen the killer dance moves of a campaigning politician? For Obama's debut appearance on the wildly popular talk show, he turned on about 30 volts of smooth charm and slid out to "Crazy in Love" with a knowing smile, stopping briefly to unload some swag on Ellen's punching bag before handily rolling back into his Chicago slide. She looked verklempt; he looked like he was trying to do the bump. "You're the, the best dancer, the, so far, the presidential candidates," stuttered Ellen. "It's a low bar," he retorted. "I'm pretty sure I've got better moves than Giuliani." We never knew what hit us. J.E.S.

9. December 7, 2007: Obama shows out for Chicago at a hometown fundraiser with Cool Kids

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In 2007, Barack Obama was merely a "presidential hopeful," and when you're a presidential hopeful, you have to drum up support and money in particularly silly ways. Like, for instance, holding a local fundraiser hosted by Jeff Tweedy, Macy Gray, and the Cool Kids. It's okay if you don't remember the Cool Kids — an erstwhile Chicago skate-and-rap duo who met on MySpace — because Obama probably doesn't either. The group's Chuck Inglish told Clash magazine that Obama greeted them by saying, "You're up-and-coming like me, that's good!" That's where the similarities in their career arcs ended. J.S.

10. March 6, 2008: Q-Tip confirms Barack Obama guest verse on as-yet-unreleased album

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"But did anyone cross-confirm with Obama?" wondered everybody who read this "Page Six" item where Q-Tip of A Tribe Called Quest insisted that "Barack is the big [guest]" on his upcoming album. "You'll see what happens, I can't reveal too much." Q-Tip's presidential album never dropped, but he later re-released "Shaka," from The Renaissance, with an excerpt from an Obama speech sampled on the intro. No original Barry verses followed, though. Maybe on the Kamaal The Abstract reissue? J.E.S.

11. April 17, 2008: Obama brushes dirt off his shoulders

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Things got ugly in the thick of the 2008 Democratic primaries. Then-rival Hillary Rodham Clinton saw her expiration date and leapt into attack mode. But in a stump speech on the campaign trail, Obama addressed her disses with some Marcy chutzpah. "You've got to expect it," he said, before letting that smooth grin shine through. "You've just gotta let it..." Then he did the infamous brush-brush motion made famous by Jay-Z's "Dirt Off Your Shoulders" video. The crowd went fucking bananas, Jay-Z no doubt got a rightful boner for himself, and you could hear the entirety of hip hop licking stamps to send in early ballots. J.E.S.

12. May 27, 2008: The Candidate tells the New York Times that bodyman "iReggie" keeps him up on rap

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Obviously, a man campaigning for President doesn't have time to manage the ID3 tags on his daily downloads from Nah Right, but he had an app for that: "iReggie," his nickname for trusted "bodyman" Reggie Love. For five years, Love was tasked with everything from dialing superdelegates to filling the Obama iPod with the latest hip-hop jams. The New York Times profiled the former Duke football player-turned-Obama personal assistant in 2008, and quoted Obama as saying, "I've gotten pretty fond of Jay-Z. He's broadened my horizons in the hip-hop world." And that's why Charlie Mack was first out the limo. J.E.S.

13. June 2008: Obama tells Rolling Stone his iPod is full of Jay-Z and Luda

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When you're running for President, every tiny thing is scrutinized. So when Rolling Stone profiled Obama for their endorsement cover, the mag's due diligence unleashed the contents of Obama's iPod to the world: Jay-Z! Ludacris! Elton John! Still mindful of his Chris Bridges beef and "rap misogyny" comments the year prior — as well as the vitality of the hip-hop generation's voter clout — he clarified his position even further: "I am troubled sometimes by the misogyny and materialism of a lot of rap lyrics, but I think the genius of the art form has shifted the culture and helped to desegregate music," he said. A diplomatic answer from a dude who emphasized "across the aisle" politicking but still wants to bump "What's Your Fantasy." J.E.S.

14. July 9, 2008: Barack references Weezy in a speech

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When Barack Obama spoke at a town hall in Georgia in the summer of 2008, Lil Wayne was the hottest name in music. "Lollipop" had made him a bona fide pop star, "A Milli" rewrote what a rap smash could sound like, and Tha Carter III was fresh off stunning the music world by going platinum in a week. Eager to keep his veneer of cool glistening, Obama told a group of kids, "You are probably not that good a rapper. Maybe you are the next Lil Wayne, but probably not. In which case you need to stay in school" — a point that he would circle back to during his presidency. J.S.

15. July 31, 2008: Obama severs ties with Ludacris after campaign song "Politics as Usual"

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The Luda/Barry love affair was deaded when the pro-Obama rapper dropped a song decrying Barack's rivals via language not suited for the Capitol steps. Aside from hanging the boringly predictable "bitch" tag on Hillary Clinton, Luda called George W. Bush "mentally handicapped," and said McCain's only worthy place in a White House chair was if "he's paralyzed." Obama, already dogged by his association with Reverend Wright (i.e., p-noid right wingers were steady freaking out), cut his Luda connection tout suite. He once again invoked the kids: "It is offensive to all of us who are trying to raise our children with the values we hold dear," said a statement issued by a campaign spokesman. "While Ludacris is a talented individual he should be ashamed of these lyrics." J.E.S.

16. May 18, 2009: Shouting out Ego Trip's The (White) Rapper Show, Obama tells a graduating class to "Hallelujah holla back!"

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One of the best contestants on Ego Trip's reality competition The (White) Rapper Show was John Brown, the somewhat lunkheaded, self-described "King of da Burbz" who nearly won the show on the strength of charm and his absurd catchphrase, "Hallelujah holla back!" Obama, addressing Notre Dame's graduating class, shouted those very words midway through his speech, leading rap-culture completists to collectively faint. Granted, that was simply the chosen name of an intramural basketball team at Notre Dame, but still, the inadvertent link from John Brown's "ghetto revival" to the White House was close enough for Ego Trip to dust off their own shoulders. "To all the haters who dismissed The (White) Rapper Show," they blogged. "Continue fronting on its impact on popular culture at your own risk." This is not a game, people! J.E.S.

17. July 16, 2009: Barack goes back to the Weezy well, references Wayne in another speech

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In a political life littered with landmark speeches, Barack Obama's 2009 appearance at the NAACP's 100th Anniversary dinner is merely a small wonder of his first term in office. But deep in the speech, he talks of the "internalized sense of limitation" that is one of the "most durable and destructive legacies of discrimination" and advises that African-American children should aspire to be more than just rappers or basketball players: "They might think they've got a pretty good jump shot or a pretty good flow, but our kids can't all aspire to be the next LeBron or Lil Wayne." Yep, we have a president who talks about good rap flows. To think we had 30 years of leaders who thought "The Carter is putting in work" meant Habitat for Humanity. J.S.

18. September 14, 2009: #ShotsFired as Obama calls Kanye West a "jackass"

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Ah, yes, the fall of 2009, when everyone had to have an opinion on Kanye West vs. Taylor Swift. Wasn't that a magical time? Even the m'fuckin' leader of the free world was asked to weigh in on this legendarily important feud, ultimately calling Kanye a "jackass." Since no sane person would argue that Kanye isn't a jackass, let's focus on the more important aspects of this pre-interview banter, like the part where Obama agreed with Kanye that Beyoncé had the better video. Or the part where he called Swift "the young lady" who "seems like a perfectly nice person." Better to be a jackass with a name, right? J.S.

19. May 5, 2010: Obama celebrates Cinco de Mayo with Pharrell and Diddy

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"Pharrell celebrates Cinco De Mayo at the White House" sounds like a completed Mad Lib answer, but instead it's just one entry on the very long list of things that Pharrell can do but you can't. Also on that list? Being hand-picked by Anna Wintour to perform at a party attended by Diddy, Usher, and Oprah, which is what Pharrell was doing a few nights before. In a photo taken at the White House, Pharrell seems pleased to be meeting the president, but he looks completely muted next to a practically beaming Obama. Maybe the prez is a big N.O.R.E. fan? J.S.

20. April 4, 2011: Pharrell gets another shot at Obama-bonding during a White House fundraiser

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At this point, we might accuse Skateboard P of photobombing, if he wasn't dressed so impeccably in every photograph. Real question: What do they talk about? And has Pharrell ever slipped a promo bottle of Qream in Obama's tux pocket? Money's on a firm maybe. J.E.S.

21. May 1, 2011: Obama shouts out 2Pac, Biggie, Ol' Dirty Bastard, Lil Jon at the White House Correspondents Dinner

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The 2011 White House Correspondents Dinner will live on in history for the infamous smirk Barack Obama flashed at an Osama Bin Laden joke just hours after ordering his capture and/or death. But even more satisfying was when the president got in multiple rap-related zingers on America's favorite truther: "Donald Trump is here tonight! Now, I know that he's taken some flak lately, but no one is happier, no one is prouder to put this birth certificate matter to rest than the Donald. And that's because he can finally get back to focusing on the issues that matter…Like, did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac?" A bonus The Apprentice one-liner invoked a Lil Jon namecheck, as well. Best of all was when he screened a parody film trailer called The President's Speech, where the bossman struggled through life without a Teleprompter. The solution to his problem is human gaffe machine Joe Biden, who was comically introduced via Ol' Dirty Bastard's "Shimmy Shimmy Ya." We give the floor to the Senator from Shaolin. J.S.

22. May 3, 2011: Michelle teaches the world how to Dougie

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Barack Obama's secret weapon is clearly Michelle, who is inarguably cooler than the President and could no doubt place high in any political run of her own. So when she executed an impeccable "Dougie" with middle schoolers during her campaign to get kids exercising and healthy, were you surprised? Don't ever ask her to twerk (show some damn respect!), but don't doubt that she could, either. J.E.S.

23. May 11, 2011: The White House invites potty-mouthed, anti-American gangsta rapper Common to the White House

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FOX News' editorial strategy in Barack Obama's first term was pretty simple: Appeal to the white conservative base by doing anything and everything to paint the president as a scary black guy turning America impure. That meant that they clung to non-controversies or, better yet, invented their own, like when they characterized one of hip-hop's least violent lyricists, Common, as a radical cop killer, when he was invited to read poetry at the White House. Yes, the same Common who titled an album Like Water for Chocolate. Yes, the same Common who is the face of Gap. This is your life as a FOX News host. J.S.

24. April 2012: Obama calls Kanye a jackass again

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Jackass Number Two: Obama is no flip-flopper, and defended his declaration of Kanye's jackassiness in an Atlantic profile, with this added dose of diplomacy: "But he's talented." J.E.S.

25. April 28, 2012: Obama shouts out Young Jeezy at the White House Correspondents Dinner

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Four years into Obama's presidency, his hair shade was slightly more salted, but so was his swagu. At a White House Correspondents Dinner, Obama quipped, "In my first term, I sang Al Green. In my second term, I'm going with Young Jeezy." Annnnd his Lambo's blue. FLOTUS shot him a look that was a combination of pride and I-wanna-sex-you-up. Jeezy responded on Twitter by saying, "you know they love the snowman in the white house." Well, they used to, at least J.E.S.

26. June 20, 2012: Barack Obama endorses Chubb Rock (sort of)

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And you thought Robocop was a shock? Way, way, way down in the B-side section of Barack Obama's Campaign Spotify Playlist; far after Electric Light Orchestra and Sugarland and Montgomery Gentry; Barack Obama plugged in Chubb Rock's 1991 monster-banger "Treat Em Right."  Well, technically, it was a very convincing Chubbs-alike from one of those wack 100 Disco Hits of the '70s and '80s comps, but just because Barry's interns fell for a counterfeit, doesn't mean his heart wasn't in the right place. In September of the same year, Michelle told an Orlando radio station that her go-to cardio jams include that song, along with Heavy D's "We Got Our Own Thang." Hip-house, you will never die! J.E.S.

27. August 17, 2012: The Don himself mispronounces "Nas"

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You know, when Obama rhymed "Nas" with "lass" on a New Mexico radio station, it could have been way worse. He could have said "2Pack," for instance. And Nas as "lass" is a logical progression from "Nasty Nas," particularly for a dude who clearly believes Jay-Z won the "Ether" beef. J.E.S.

28. Sept 2, 2012: Obama video-bombs Jay-Z's inaugural Made in America festival

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How often can Jay-Z continue to one-up himself? He has appeared on magazine covers with Warren Buffet, is part owner of an NBA team that moved to his borough, and named his daughter after a color and a plant. How about introducing the headlining set at his own summer festival with a video message from the president saying that Hov is what "Made in America" means? Yes, that'll do. J.S.

29. September 6, 2012: The official Obama campaign Tumblr samples Run-DMC

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Bootleg "RUN DNC" T-shirts, a parody of one of hip-hop's most iconic logos, have been floating around since the 2008 election. But only in 2012 did they hit Obama's official Tumblr, posted to commemorate the latest Democratic National Convention — with Obama, Biden, and Bill Clinton cast as Jam Master Jay, Rev Run, and DMC. Co-signing this rap/politics merger was more proof that Barry O's the true king of rock. And, perhaps most importantly, that his campaign staff understands the Internet generation, memes, and highly rebloggable social media better than any politician before or since. Who's the man? J.E.S.

30. September 8, 2012: America's rap genius deconstructs Nicki Minaj's Mitt Romney "endorsement"

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A contentious election season, two months before voting day. A famous rapper known for outrageous delivery and outrageous hyperbole says in a song, "I'm a Republican voting for Mitt Romney / You lazy bitches is fucking up the economy." Amazingly, many in the media actually believe that said rapper was, in fact, endorsing Romney. Of all people, the President of the United States of America had to clear the air on a rap radio station, joking, "That was probably Roman who did it." The rapper confirms via Twitter: "Thank you for understanding my creative humor & sarcasm Mr. President, the smart ones always do." And he didn't even need the Internet to annotate the lyric: the sign of a true hip-hop fan. J.E.S.

31. Sept. 11, 2012: Obama talks Flo Rida and Pitbull

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Barack Obama is nothing if not incredibly savvy at maintaining his cross-demographic appeal. So how did he open his interview with legendary Miami bass DJ, rapper, and radio personality DJ Laz? By turning it right round and putting himself at a level below real stars like Pitbull and Flo Rida: "I'm the one who should be humbled. You're big time. You've got Pitbull and Flo Rida and all these guys just beating a path to your door. And so I'm hoping for a little of that magic from you in this interview." You know you want him! J.S.

32. Sept. 18, 2012: Jay and Bey visit the White House, initiate bonus shoulder-brushing

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What is YOLO-er than brushing your shoulders off? Brushing them off with Jay-Z and Beyoncé themselves at the 40/40 Club. Speaking at a fundraiser held by the hip-hop royal couple, he says, "I was gonna just 'drop the mic' but I decided that would be inappropriate." J.E.S.

33. October 15, 2012: The Nobel Peace Prize winner mediates the Nicki Minaj and Mariah Carey feud

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Mimi and Minaj had been going at each other's throats pretty heavy on the American Idol set, so logically, a radio DJ in Florida, the country's most important swing state, used valuable airtime with a campaigning incumbent to ask about the feud. Obama, always up on the latest in beef, was very Presidential in his answer: "I think that they are going to be able to sort it out," he said. "I am confident. I'm all about bringing people together." He then shouted out Minaj (on his iPod), Mariah (sang at some events for him) and Nick Cannon-Carey (who doesn't love Nick Cannon?) J.E.S.

34. October 26, 2012: Obama tells Sway that hip-hop is "most vibrant [political] musical art form right now"

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When rapper-turned-DJ-turned-MTV-host Sway Calloway asked Obama to name contemporary artists who uphold the standards of politics and music in the mold of Bob Marley and Public Enemy, Obama makes a swift dodge — he's obviously not overly concerned with downloading, like, Immortal Technique mixtapes this close to the election, nor can he point Sway to his obscure political rap Tumblr (yet). But Obama's response was as thoughtful and on-point as anyone who's well-versed in music culture: "I think the most vibrant musical art form right now, over the last ten, 15 years, has been hip-hop. And there have been some folks that have dabbled in political statements, but a lot of it has been more cultural than political." We're pretty bummed he didn't rip open his button-up at that moment to reveal a Diddy "VOTE OR DIE" t-shirt, but c'est la vie. J.E.S.

35. October 29, 2012: Obama reveals that his iPod also bangs Fugees, Eminem, and Gil-Scott Heron on the reg

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Four years later, Obama opens his iPod a second time, and we can see the evolution of his rap preferences. He stuck with Jay-Z through the whole "Young Forever"/Mr. Hudson thing, listens to Eminem, and rides for the edifying works of Fugees and Gil-Scott Heron. Mr. President, can you maybe pardon Lauryn Hill then? J.E.S.

36. November 5, 2012: Jay-Z invited to perform a "bitch"-less "99 Problems" at Obama's final campaign rally

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Remember when Blue Ivy was born, and someone circulated a poem Jay-Z supposedly wrote declaring that he would stop saying the word "bitch" in his music now that he has a daughter? That was a hoax. Blue Ivy's birth did not inspire a moratorium on the b-word in Jay's vocabulary. Who did? Barry O, obviously, when Jay replaced "bitch" with "Mitt" in the chorus of "99 Problems" for Obama's final campaign rally of the 2012 election — and he looked like the happiest man on the entire planet while he was doing it. Because Barack Obama is magic. Sorry magic baby Knowles-Carter. Give it a couple years. J.E.S.

37. January 17, 2013: Nobody Beats Nick Cannon and the Biz on Obama's Inauguration Playlist

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President Obama may take calls from Jay-Z and walk around rapping Young Jeezy, but his second inauguration playlist featured only one rap song...and it was by Nick Cannon. Cannon's "My Mic" is as perfectly generic and "inspirational" as you would guess (even though we swear he says "P-popper" in it), with a chorus where Cannon asks himself, "What would I be without my mic?" The answer is apparently "a reality TV show host and husband of Mariah Carey," so good for him. Bonus points to both Obama and Cannon for the guest beatboxing on the track supplied by the one and only diabolical Biz Markie. J.S.

38. April 11, 2013: The White House Press Secretary Ethers Jay-Z Song

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On April 11, Jay-Z released "Open Letter," a 2:41 two-verse SoundCloud... and the White House responded to it like it was Wikileak'd North Korean nuclear secrets or something. In the song, Jay-Z boasts that he got "White House clearance" to visit Cuba to chill on the beach and smoke cigars and wear white fedoras. Despite the fact that this is the man who once claimed he ejaculated in Nas' Jeep in a song, White House press secretary Jim Carney still denied the claim at a press briefing: "I guess nothing rhymes with Treasury," he said. "The White House, from the president on down, had nothing to do with anybody's... travel to Cuba. That is something that Treasury handles." C.W.