President Barack Obama tapes an appearance on the Late Show With David Letterman in New York City May 4, 2015. The president and first lady appeared many times on the show, but Obama’s Sept. 10, 2008, appearance was one of the most memorable.
NICHOLAS KAMM/AFP/Getty Images

David Letterman’s retirement from his long-running Late Show With David Letterman—which began on Feb. 1, 1982, as Late Night With David Letterman on NBC and later moved to CBS on Aug. 30, 1993, after NBC chose Jay Leno to succeed the legendary Johnny Carson on The Tonight Show—has rightfully prompted a lot of celebration.

Back in 2013, Letterman hit a milestone, surpassing his mentor-friend Carson, who had held the record for longest-serving late-night TV talk show host at 31 years. Given the nature of today’s television landscape, it is unlikely that anyone will surpass the 33-year record set by Letterman, whose many big breaks prior to Carson’s mentorship included writing jokes for Jimmie Walker, of Good Times fame, with the likes of Paul Mooney and Leno.

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With May 20 marking his last show and the ending of an era, The Root has compiled 10 memorable moments featuring black guests over Letterman’s last 33 years.  

1. Oprah Winfrey

Her Dec. 1, 2005, appearance—the first since May 2, 1989—in support of The Color Purple’s run on Broadway ended a reported 16-year feud that Letterman often joked about. It is the late-night host’s fourth-most-watched episode.

2. Barack Obama

Although the numerous appearances that the president (and first lady Michelle Obama) made on Letterman after his historic election offer many choices, his appearance as the Illinois senator (his second) running as the Democratic presidential nominee on Sept. 10, 2008, about two months before his historic victory might be the most memorable.

3. Janet Jackson

Her exclusive conversation with Letterman on March 29, 2004—her first after the infamous Super Bowl “nipplegate” incident—may have been awkward for Jackson, but it is certainly one that stands out.

4. Eddie Murphy

The quality of the broadcast posted on YouTube may be questionable, but there’s little denying that Murphy’s Dec. 17, 1984, appearance to promote Beverly Hills Cop is a gem, especially when Murphy speaks of his return to Saturday Night Live as host.

5. Sean “Diddy” Combs

Although Puff Daddy/Diddy has appeared on Letterman numerous times in various capacities, even hosting Letterman’s legendary top 10 list, this one on July 23, 2009, in which he talks about Michael Jackson attending one of his infamous parties in search of Beyoncé, stands out.

6. Halle Berry

This early Berry appearance on March 14, 1995, to promote the film Losing Isaiah when Berry was married to baseball player David Justice is still an interestingly strange one.

7. Dave Chappelle

Since leaving his top-rated Comedy Central show in 2005, Chappelle has rarely discussed the infamous incident, but yet he opened up to Letterman on June 10, 2014.

8. Denzel Washington

Almost always in a class by himself, Washington made Letterman history when he served as the sole guest with no studio audience during Hurricane Sandy on Oct. 30, 2012, to promote his film Flight.

9. Paul Mooney

Sadly, Richard Pryor’s Jan. 15, 1987, appearance on Letterman can’t be found on YouTube, but when Mooney appeared on Letterman on March 27, 2007, he and Letterman referenced their mutual friend while discussing Michael Richards’ infamous n-word breakdown, Bush, gas prices, Hilary Clinton and more.

10. Jay Z

Some have observed that Jay Z may have been under the influence during this Sept. 9, 2009, appearance, but this exchange with Letterman, especially in reference to Jay Z’s marriage to Beyoncé, is humorous.

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Ronda Racha Penrice is a freelance writer living in Atlanta. She is the author of African American History for Dummies.