Image via Complex Original
26.
Hip-hop is probably one of the last things that comes to mind when you think of the 68-year-old David Letterman, but the genre has a surprisingly great history on The Late Show. Appearances were scarce in the opening and closing years of the show (especially the latter), but for a time Letterman showed love to some of the best MCs in the game—up-and-coming and already established. The 2000s were particularly lush, with multiple performances from the likes of Jay Z, Kanye West, OutKast, and more. As we prepare for Letterman to go off the air after more than 30 years, we're celebrating his storied career the best way us hip-hop heads know how by counting down the best acts he's welcomed on the show.
Ian Servantes is a writer living in Colorado. Follow him @ian_servantes.
25.Tyler, the Creator f/ Earl Sweatshirt and Domo Genesis “Rusty”
Date: April 4, 2013
Is this a hip-hop act or comedy? Because it's hard to stop laughing at Tyler and Earl's moves, Domo Genesis saying homie 600 times, and the whole crew dipping out, leaving old man Letterman to think he has to end the show alone.
24.Ginuwine f/ Missy Elliott “Get Involved”
Date: July 23, 2009
Missy Elliott is the Queen, and we should all kiss the ring if we forgot it for even a second before her Super Bowl performance earlier this year. This Letterman performance isn't even from her peak and it slays.
23.Busta Rhymes Medley
Date: Aug. 23, 2006
Busta Rhymes treated this like a real concert. He catered to the real-life audience instead of the much larger one at home, making it even better for the latter.
22.Black Eyed Peas “Let's Get It Started”
Date: May 20, 2004
Here's a reminder that the Black Eyed Peas weren't always so annoying and that Taboo has always been ghoulish.
21.The Black Keys f/ Mos Def and Jim Jones “Ain't Nothing Like You (Hoochie Coo)”
Date: Dec. 8, 2009
Take this as an oppurtunity to revist Blakroc, a supremely underrated collaboration between the Black Keys and a group of rappers. If Mos Def toured with the Black Keys it'd be the most lit rock tour of the 2000s.
20.Eminem and Jay Z “Not Afraid” and “Renegade”
Date: June 25, 2010
I don't know why Jay Z would perform live the song on which Eminem murdered him on his own shit, but I'm sure glad he had the humility (or a false sense of who did the murdering) to allow this to happen.
19.J. Cole “Be Free”
Date: Dec. 10, 2014
J. Cole delivered a topical, heartbreaking, minimalist performance of the song he recorded in response to the murder of Michael Brown. This is one of the best musical expressions of frustration from the wave of police killings that are still plaguing this country.
18.Kid Cudi “Pursuit of Happiness”
Date: Sept. 11, 2009
This is what triumph looks like. Cudi was just days away from releasing his debut album, and you can see the joy radiating as his grin is plastered on his face for the entire performance backed by Ratatat.
17.Kanye West “Love Lockdown”
Date: Nov. 24, 2008
It's a shame Kanye hasn't performed on Letterman since 2009 (you'll see that performance later). Dude brought two stories of drummers and lights this time. Imagine what he'd pack into the Ed Sullivan Theater now.
16.The Roots f/ Chrisette Michele and Wale “Rising Up”
Date: April 28, 2008
After shining with the Roots on Letterman, Wale has never opted out of performing with the band on his Fallon appearances. They bring out the best of everyone.
15.Lupe Fiasco “Superstar”
Date: Jan. 2, 2008
Remember pre-conspiracy Lupe? That was the best Lupe, even when he made his most transparent crossover hit with a replica of Adam Levine.
14.Beastie Boys “Sabotage”
Date: Aug. 4, 1994
Fly, fresh, dope, and fat. Those are the words Letterman used to describe a group that would go on to kill it on his show on numerous occasions. Ad-Rock smirked during this screamer of a performance like he could see the future.
13.The Roots “Here I Come”
Date: Aug. 29, 2006
This song would go on to become the theme of a rival late-night talk show. The Roots' pre-Fallon performances were the best audition tapes.
12.Jay Z “Roc Boys”
Date: Nov. 2, 2007
Dare we say this is better than the studio version? Those live horns and Hov's in-person charisma brought an unmatched intensity.
11.Nelly “Hot in Herre”
Date: Aug. 28, 2002
No one in their right mind would have guessed Nelly's strip club anthem could be heightened with a groovy live-band arrangement. Yet here we are watching the St. Lunatics killing it in front of a full band. Weren't the early 2000s weird?
10.Kanye West f/ Syleena Johnson “All Falls Down”
Date: Feb. 16, 2004
Maybe it's just nostalgia, but it's hard to resist this early Kanye performance. I'll never complain about angsty Yeezus Kanye, but it's refreshing to see him loose and smiling in a performance that can only be called modest with hindsight.
9.Lupe Fiasco f/ Jill Scott “Daydreamin'”
Date: Nov. 11, 2006
Lupe Fiasco was once one of the most talented kids in the game. Putting heavy-hitter Jill Scott and a string section on his side was like handing him performance-enhancing drugs.
8.Jay Z f/ Mary J Blige “Can't Knock the Hustle”
Date: April 4, 2008
Only the coolest dude alive could pull off performing the third single from his least commercially viable album on Late Night. New, washed Hov songs can never erase his ability to crush it with the classics—which we just saw this past weekend with his Tidal concert.
7.OutKast “Roses”
Date: May 30, 2004
OutKast really performed a '50s-inspired hip-hop musical ending with a full-out brawl on Letterman. We are not worthy.
6.Keri Hilson f/ Kanye West “Knock You Down”
Date: May 4, 2009
Much like the song itself, if you only fuck with the Kanye performance, you're basic. By the time Yeezy makes an appearance Keri Hilson has already captivated with stellar choreography and chops to match. That 2009 Kanye swagger is just a bonus.
5.Mos Def “Quiet Dog”
Date: June 8, 2009
You can't see his eyes, but it still feels like MosDef is staring into your soul as he methodically pounds on the drums and tears his way through his god-like verse.
4.Busta Rhymes Medley
Date: Aug. 23, 2000
Busta Rhymes' on-stage presence is matched by few in hip-hop. His eyes are ready to pop out of his dome, his every movement is exaggerated, and he's been blessed with a commanding baritone. Dude could steal the stage with two of the most legendary hip-hop groups right there with him.
3.Fugees f/ A Tribe Called Quest and Busta Rhymes “Rumble in the Jungle”
Date: June 26, 1996
Lauryn Hill, Pras, John Forte, Wyclef Jean, Q-Tip, Phife Dawg, and Busta Rhymes. On one stage. On national television. Enough said.
2.OutKast “Hey Ya”
Date: Sept. 26, 2003
This song was undeniably unfuckwitable everywhere it went—TRL, the Grammys, Letterman, and to this very day at weddings where brides and grooms fail to see the irony. Even Letterman couldn't take his eye off of Andre 3000, and not just because of his hot pink jacket. The host had no problem playing favorites with his musical guests. Those who simply showed up got a simple, “Hey, how you doing?” But those who truly brought it got a greeting similar to Andre's: “Boy, I enjoyed that. That was very nice.”
1.Beastie Boys “Ch-Check It Out”
Date: June 15, 2004
Nearly 10 years after first appearing on The Late Show to perform “Sabotage,” the Beastie Boys returned to prove they hadn't lost a step as they sauntered through New York City and into the Ed Sullivan Theater. Their energy was as palpable as ever while executing a flawless alternative to the standard late-night talk show performance. It's only fitting that the trio was one of the most storied musical guests of Letterman, himself an alternative to stuffier predecessors.