The 8 Blackest âLettermanâ Moments [VIDEOS]<br />

The leader of the free world yuks it up with Letterman

Recent announcing to the world that he would retire next year, David Letterman—the longest-serving late night host in TV history—wasn’t only responsible for provocative interviews with Drew Barrymore and Madonna; he’s also credited for booking some of the most influential African-American leaders and entertainers ever. Known for his brilliant comedic talent and compelling personality, just about all of African-American culture has fallen for the gap-toothed comedian.

Here’s eight great moments in Black culture from Late Show with David Letterman.

Oprah Winfrey vs. David Letterman

David Letterman is a man of humorous words, but his jokes weren’t always so funny, especially to media mogul Oprah Winfrey. Stemming from a joke he once made about Oprah and her Color Purple role (and, strangely, actress Uma Thurman), a feud between Winfrey and Letterman went on for many, many years. Winfrey told Time magazine she wouldn’t go on his show because she’s been “completely uncomfortable” as the target of his jokes. However, it all came to end when the O dropped by Letterman’s quarters in 2005, making good with the late-night host. “Could you tell me please what has transpired?” Winfrey asked Letterman. “I have never for a moment had a feud with you.”

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Barack Obama’s first appearance as president

When you’re Letterman, everyone’s making a booking… even the president. Making his first appearance after winning the 2008 election, President Obama visited the hallowed halls of the Ed Sullivan Theater (the first time since 1993 that a sitting president appeared on the Late Show). Addressing several topics—including race and political structure—the result was a record-blowing ratings night and the introduction of a new “cool” president.

Janet Jackson, post-Nipplegate

Sure, David Letterman lords over a male-dominated industry. But that doesn’t mean he doesn’t come to the defense of beautiful women, especially a Black woman like Janet Jackson. In the midst of damage control after her infamous 2004 Super Bowl half-time performance, the coy, soft-spoken Janet pleaded with Letterman to not talk about “Nipplegate,” but Letterman wouldn’t hold back. “When things are bad, it’s always important to have someone to blame,” Letterman said. “That’s why I believe it’s this Timberlake guy [to blame].”

Denzel Washington’s N-Word Slip Up

Denzel Washington is vehement about community outreach, and for that he’s allowed a little slip-up here and there—only when on Letterman. This was the case when the two-time Oscar winner blurted out the N-word unintentionally while discussing unemployment. While Washington made a mistake slipping up, we’ve learned that the charisma of Letterman is enchanting enough that you can talk with him any way you want to—but you gotta remember, he’s not the only one listening.

Michelle Obama’s first appearance: “Don’t make me cry”

Late Show with David Letterman is not for the faint-hearted, and the FLOTUS is no exception the rule. In fact, she’s hip to it. When Letterman asked Obama about her father, a crack in her voice wavered as she spoke highly of the late Fraser C. Robinson III. But immediately recognizing her surroundings, she quickly snapped out of it. “Don’t make me cry,” Obama said. “This isn’t Oprah, it’s supposed to be Letterman. What’s up! Where are the laughs?”

Beyoncé’s “Crazy in Love” performance

Jimmy Fallon may tug at the purse strings of pop culture, booking musicians like Frank Ocean and employing The Roots as in-house musicians. But that’s because he’s taken cue from his predecessor Letterman, who’s  featured many megastars over his three decades on TV: like, for example, Beyoncé. Donned in a flesh-toned, silk, form-fitting ensemble, along with a full-band and four dancers, Letterman allowed Beyoncé to take control on the solo tip. Her classic “Crazy in Love”—complete with echoing guitar and vocals riffs and her infamous, alluring “uh-oh” dance—marks one of her best televised performances of the track.

Kanye West’s “All Falls Down,” with John Legend and Syleena Johnson

Back before Kanye West was able to vocalize his frustrations with the media on Jimmy Kimmel Live, he once revealed his narcissistic addiction to fresh with “All Falls Down” on Letterman. Dipped in a sky-blue Polo sweater, whipped-cream white pants and a dangling gold Jesus piece, West eloquently emceed about retail-ridden insecurities alongside John Legend, a wailing Syleena Johnson and violinist Miri Ben-Ari. There’s even that trademark College Dropout mascot in background! The good ol’ days, thanks to Letterman.

Lupita Nyong’o speaks pre-Oscar about Oprah and Charlie Brown

Several factors attribute to the success of the ravishing Lupita Nyong’o: Charlie Brown, Oprah and a wild imagination. David Letterman, not so much. But two weeks before her Academy Award win, Letterman sat down with the 12 Years a Slave actress discussing her childhood and influences. When Letterman asked Nyong’o if he was influential to her success, Nyong’o smiled and graciously, honestly answered, “Not really.” Well, at least Letterman can say he interviewed one of the most beautiful women of the ’10s.