The Presidential Suite: A Look Back at Obama’s Musical Milestones

From poking fun at Kanye West, to curating playlists, to singing with Willie Nelson, to hosting the recent South by South Lawn festival at the White House, President Obama has taken advantage of his musical know-how in unprecedented ways.
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*’Cause I’m black and I’m proud
**I’m ready and hyped plus I’m amped
*Most of my heroes don’t appear on no stamps

Chuck D’s gruff protest turns ironic as “Fight the Power” blares across the White House grounds. On a bright October afternoon, over manicured grass and against neo-classical columns, Public Enemy’s 1989 polemic plays as a sly, surreal soundtrack to the preparations for South by South Lawn, the Obama administration’s riff on Austin’s annual multimedia showcase, South by Southwest. Stagehands are snaking cords across a platform dense with speakers and LEDs. Tech entrepreneurs are buffing virtual reality headsets and firing up whirring robotics. President Obama himself is perusing the scene too—he strides over to a bench, sits down next to a life-sized Lego man sculpture, and pantomimes a deep conversation with it before ambling back into the Oval Office, chuckling Secret Service in tow.

Billed as the White House’s first “festival of ideas, art, and action,” SXSL feels idyllically removed from the present political tire fire, a fitting event for the president who made optimism chic again. It’s a mellow, unpretentious affair where music permeates the surrounding austerity; the funk-rockers Black Alley stake out an East Wing hallway, strutting under solemn oil paintings of statesmen past, and the R&B singer Gallant wails melisma in the East Room, 10 feet from where Obama announced the death of Osama Bin Laden. Near the Rose Garden, kinetic visual artist David Garibaldi blasts a brassy soul beat and leaps with balletic-meets-breakdance athleticism while slapping paint to canvas, the seemingly random smears slowly cohering into a portrait of the president. When he begins around the ears, the woman next to me yells, “I know who it is!”

Out on the mainstage, Common makes an unannounced appearance, rapping about the racial injustices of the prison system; he’s later spotted chatting with Obama senior advisor Valerie Jarrett. At sunset, before the amiable folk-poppers the Lumineers play “Stubborn Love”—which Obama included on his 2015 summer playlist—singer Wesley Schultz points to the White House’s second floor and urges the crowd to stand and sing along. “[Obama] said he might be watching from that balcony,” Schultz drawls, “so let’s make sure.” Even Trent Reznor, seated behind me, clambers out of his seat but abstains from singing the chirpy chorus—an act of diplomacy unto itself.

In total, SXSL feels like the climax of all the cultural cachè Obama has accrued over the past eight years—his many examples of pop fluency deployed as populist outreach. Releasing hip-hop- and rock-heavy playlists on Spotify, joining Lin-Manuel Miranda in a Rose Garden freestyle, combining forces with Jay Z and Beyoncé on a fairly regular basis—these were all anomalously cool efforts for a commander-in-chief. He’s proven to be more musically perceptive than any other president—even the timbre of his oration suggests a man who deeply appreciates the joys of melody and rhythm.

President Obama has quoted Jay Z and slow danced to Beyoncé during his tenure.

The road to SXSL began in March, when Obama stopped by South by Southwest for a keynote discussion on encryption and civic responsibility (and a hearty endorsement of Austin’s tacos). The appearance was spurred on by Jason Goldman, a former Twitter and Google executive, who joined the White House last April as its first chief digital officer. Goldman then spearheaded SXSL across the last seven months—first mining the president’s playlists for artists, then opening a public nominations process for attendance. Ultimately, 2,500 artists, entrepreneurs, and cultural organizers were culled from over 20,000 entries.

Cloistered in the Jacqueline Kennedy Garden, Goldman tells me, “The real success of this event will be if in six months or a year, someone’s like, ‘Oh, that’s [something] I saw for the first time at South by South Lawn.’ It could be a product, a nonprofit, an artistic movement.” He grins. “If someone forms a band, that would be great.”

Along with SXSL’s musical attractions, attendees try out interactive exhibits aimed at sustainability, sample organic snacks, and surreptitiously snap photos of roving celebrities—Ron Howard, Hannibal Buress, the “Stranger Things” cast. (I’m informed breathlessly by one attendee that, ahead of his keynote panel with Obama, Leonardo DiCaprio has been spotted vaping.) The atmosphere is professional—nary a fringed vest in sight—but even the White House staffers are a bit giddy; Goldman and his colleagues slap palms at they pass, lilting “It’s all happening!” to each other, a là Almost Famous.

Some of South by Southwest’s organizers are also onsite, but off the clock. SXSW co-founder Roland Swenson, 60, says, “This is incredibly exciting for us, and certainly not something that we ever expected to be part of.” He chuckles. “Before Obama, we tried to get Bill Clinton. But then he got in trouble.”

I ask Swenson if he finds Obama’s pop-culture savvy to be noteworthy for a politician. “He’s a product of his time and place and generation, so he was going to be more music-savvy and media-savvy than his predecessors,” he says. “I think it’s more a function of his personality as opposed to a strategy to win votes. He’s just always been a very inquisitive person, curious about music and art and ideas. That’s what we’re seeing here today.”

The Lumineers’ Schultz seems pleasantly bewildered by his surroundings. “I can’t picture any other president doing something like this,” says Schultz. “I feel like Obama’s participated in a lot of things that the average president wouldn’t even touch.”

SXSL’s evening keynote involves the president in conversation on global warming with DiCaprio and the climatologist Dr. Katharine Hayhoe. The Washington Monument looms stage left, two flashing red lights illuminating the peak, as if to stare down reproachfully while they stress the peril of carbon emissions.

Looking across the field at the rapt expressions directed at the president (not least from DiCaprio), I’m reminded of a moment eight years ago, to the month: A rainy afternoon in rural Pennsylvania when, as a volunteer coordinator for the Obama campaign, I was midway through a tough canvassing sweep in a very red industrial town. My team and I were sullen, bedraggled from both the downpour and succession of Sarah Palin zealots. We ducked into a tavern; the bartender scowled at our muddied forms, and we braced for our next showdown of the day.

He strolled over and spied our clipboards. “You’re with Obama?” he asked. We nodded wanly. He slid some shots our way, flicked at his iPod, and Stevie Wonder’s “Signed, Sealed, Delivered I’m Yours”—the Obama campaign’s theme song—filled this sudden sanctuary.

“He’s got good taste in music,” the bartender said. “It’s not everything, but it sure isn’t nothing.”

The president has had a contentious public relationship with Kanye West over the years—like the time he denied calling West on the phone, shutting down the rapper's boasts.

In honor of his golden ears, here’s a timeline of Obama’s most notable music moments from the last eight years:

April 17, 2008

During the presidential primaries, Obama makes headlines for evoking the hip-hop hierarchy. While campaigning in North Carolina, he shrugs off criticisms from his Democratic opponent Hillary Clinton, saying, “You just gotta…” with a Jay Z-esque brushing of the dirt off his shoulders.

Dahlak Brathwaite, a 30-year-old performance artist and SXSL attendee, calls Obama’s interest in rappers “legitimizing” to his work. “It feels like there’s an acceptance of hip-hop culture that wasn’t there before,” he says. “When he says, ‘I like Mozart—but I like Kanye and I’m a Jay Z fan, too,’ that spotlight adds some credibility and class to hip-hop that wasn’t there before.”


June 25, 2008

Obama name-drops Ludacris as a musician on his iPod (alongside Bob Dylan, Miles Davis, and Sheryl Crow). Soon after, he has to drop Luda himself when the rapper releases “Politics as Usual,” a pro-Obama track in which he calls Hillary Clinton a “bitch.”


July 9, 2008

Obama shows off his Weezy acumen at a town hall meeting in Georgia. “You are probably not that good a rapper,” he tells the teens in the audience, not unkindly. “Maybe you are the next Lil Wayne, but probably not—in which case, you need to stay in school.”


January 20, 2009

Beyonce performs Etta James’ “At Last” at Obama’s presidential inauguration.


May 12, 2009

Lin-Manuel Miranda performs at the White House Poetry Jam, during which he debuts a work-in-progress that will become the opening song of Hamilton. Evan Ryan, the Assistant Secretary of State for Educational and Cultural Affairs, remembers that evening well. “[Miranda] said he was going to test out something about Alexander Hamilton,” recalls Ryan, who oversees Obama’s cultural exchange programs, including Fulbright scholarships and American Music Abroad. “Everybody sort of chuckled. And then he did it, and everybody was like, ‘Wow, this might be something.’”


September 14, 2009

After Kanye West stage-crashes Taylor Swift’s speech at the MTV Video Music Awards, Obama calls West a “jackass” in an off-the-record portion of an interview with CNBC. In March 2015, he burns Ye again: During an appearance on “Jimmy Kimmel Live!” Obama denies calling West on the phone, contrary to the rapper’s recent boasts otherwise. “I don’t think I’ve got his home number,” the president deadpans.


May 5, 2010

Pharrell, wearing a tuxedo and spiffy monogrammed slippers, celebrates Cinco de Mayo with Obama at the White House.


April 30, 2011

At the White House Correspondents’ dinner, Obama references hip-hop’s ’90s East Coast-West Coast rivalry while jabbing back at Donald Trump’s persistent “birther” accusations. “Donald Trump is here,” he quips onstage. “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?”

Obama ridiculed Donald Trump's "birther" campaign back in 2011 with a pointed reference to the mysteries surrounding the deaths of Biggie and Tupac.

May 2011

The president and first lady invite Common to the White House for the slam poetry showcase “An Evening of Poetry”—the first since a similar event organized by Laura Bush in 2003 was criticized and ultimately abandoned after certain poets declined or threatened to protest the war in Iraq. Right-wing pundits latch onto the rapper’s “Letter to the Law”—specifically, the line “Burn a Bush ’cause for peace he no push no button”—as proof of Obama’s own insurrectionist agenda. White House press secretary Jay Carney shrugs off the accusations, and Common performs.


January 20, 2012

President Obama sings a few lines of Al Green’s “Let’s Stay Together” during a fundraiser at the Apollo Theater. Despite holding the tune, he adds to Green, “Don’t worry, Rev, I cannot sing like you, but I just wanted to show my appreciation.”


February 9, 2012

Obama releases a reelection playlist heavy on indie rock and R&B, featuring Arcade Fire, Jennifer Hudson, Raphael Saadiq, and No Doubt. “I swear it is him who makes the playlists,” insists Goldman. “He has personally selected all of those songs and writes them out by hand. He really loves a diverse range of music.” While compiling his summer playlists, Obama couldn’t condense his picks to the staff’s recommended 20, Goldman says, so he had to expand to “Day” and “Night” selections.


February 22, 2012

At the White House Blues Festival, Obama lifts the mic from Mick Jagger to sing “Sweet Home Chicago” with B.B. King.

The president showed off his singing chops alongside B.B. King in 2012.

April 24, 2012

Obama “Slow Jams the News” with Jimmy Fallon and the Roots on “The Tonight Show” to promote his message to Congress about not increasing student loan rates. Black Thought can barely contain himself as the “Barack Ness Monster” intones about Stafford loans atop the playfully sleazy beat.


September 1, 2012

President Obama appears by satellite during Jay Z’s set at the first Made in America Festival in Philadelphia. During “PSA,” he beams in for a surprise address, urging the audience to vote. He also extols Jay: “No matter who you are, what you look like or where you come from, you can make it if you try. Jay Z did. He didn’t come from power of privilege,” he says. “He got ahead because he worked hard, learned from his mistakes, and just plain refused to quit.”


February 22, 2013

FLOTUS shows her pop chops, too; she does the Dougie—very well—on “Fallon.”

Barack isn't the only Obama with rhythm—Michelle busted out some classic mom moves with Jimmy Fallon in 2013.

April 27, 2013

Jay Z continues to loom large. During Obama’s speech at the White House Correspondents Dinner, he references Jay and Beyoncé’s much-decried vacation to Cuba. “Some things are beyond my control. For example, this whole controversy about Jay Z going to Cuba—it’s unbelievable,” he says dryly. “I’ve got 99 problems and now Jay Z’s one.”


November 7, 2014

During a PBS salute to the troops, Obama joins Willie Nelson in a rendition of “On the Road Again.”


June 16, 2015

After the Charleston mass shooting, Obama delivers the eulogy for the Reverend Clementa Pinckney. Visibly tearful, he breaks into a verse of “Amazing Grace” and is joined by those in attendance.


August 14, 2015

Obama releases his summer playlist, the “Day” version of which includes Aretha Franklin, Howlin’ Wolf, Florence and the Machine, and a major wildcard: the cult barroom-boogie rockers Low Cut Connie. “I woke up that morning in Philly and had hundreds of texts and tweets,” recalls Low Cut Connie frontman Adam Weiner. “I clicked on Twitter and it said, like, ‘POTUS Playlist hahaha Low Cut Connie. I can’t believe it.’ And I thought, What the hell is POTUS? Then I’m brushing my teeth and I’m like, Isn’t that the president?

Weiner was so grateful, he wrote a thank-you letter to Obama. The following spring, he was invited to the White House, where he and his wife met the president and were given a tour of the East Wing by Pete Souza, the White House’s official photographer. On the wall, he saw a series of photos of Prince, one of Obama’s faves, giving a secret performance at the White House in 2015. As Weiner recalls, Souza revealed that the day Prince died, Obama asked him to print some of those photos and hang them in memoriam.

“One image is President Obama and he’s got his jacket off, his sleeves are rolled up, and his tie is half undone, and he has his arms up in the air, with a huge smile on his face,” says Weiner. “Next to him, Prince is playing guitar and looking at him—only Prince could give this face—like, ‘I’ve got the president acting like a fool onstage.’ President Obama just looks like a fanboy. He’s like, ‘I got Prince to play a private concert in my house. And victory is mine.’”


March 2016

Both Barack and Michelle Obama deliver keynotes at SXSW—POTUS on technology and civic responsibility, FLOTUS on her “Let Girls Learn” initiative. Ahead of her appearance, Michelle unveils the charity single “This Is for My Girls” with Missy Elliott, Janelle Monaé, Kelly Clarkson, Zendaya, and others. (The first lady and Elliott also bust it out a few months later in James Corden’s “Carpool Karaoke” series, along with a zippy take on Elliott’s “Get Ur Freak On” and Stevie Wonder’s “Signed, Sealed, Delivered I’m Yours.”)


March 15, 2016

Lin-Manuel Miranda returns to the White House to freestyle in the Rose Garden as Obama prompts him with political cue cards. “They’re talking about things that are germane, but they’re doing it in a new way, in a context that is obviously very tied to the presidency and the administration,” Goldman says.

After debuting what would become the opening song of his musical Hamilton at the White House in 2009, Lin-Manuel Miranda returned for an off-the-dome freestyle session with the president earlier this year.

April 16, 2016

Obama invites a host of hip-hop stars—including the once-shunned Ludacris—to the White House to discuss his My Brother’s Keeper support program for young men of color affected by racial injustice. Common, who was in attendance that day, recalls: “It was myself, A$AP Rocky, Rick Ross, J. Cole, Chance the Rapper, and many more in this room, and I’m looking at a picture of George Washington with the President right there next to me, and I’m like, Man, I know George Washington never would’ve seen this many brothers in the White House!


April 30, 2016

At his final White House Correspondents’ Dinner, the president airs “Couch Commander,” a parody video of his impending retirement. The clip includes Joe Biden polishing his aviators, John Boehner weeping over Toy Story 3, and an unexpected soundtrack: Wiz Khalifa’s “Cameras.”


July 4, 2016

Obama invites Kendrick Lamar, his professed favorite rapper, to the White House Fourth of July BBQ. Lamar performs (censored) versions of “Alright,” “Bitch Don’t Kill My Vibe,” and joins Obama and Janelle Monaé in singing “Happy Birthday” to Malia Obama.


August 11, 2016

Obama drops his second annual summer playlists. Wale, the Beach Boys, and Courtney Barnett make the “Day” cut; D’Angelo, Chance the Rapper, and Billie Holiday top the “Night” list.


October 3, 2016

The White House hosts its first (and, with a fraught election looming, potentially last) South by South Lawn festival.