Stephen Colbert's Five Greatest Musical Moments

This week, fans of funnyman Stephen Colbert had their nine month drought of truthiness come to an end as his Late Show with Stephen Colbert premiered on CBS. With Colbert as sharp as ever, his brand of comedy remained despite him casting off the restrictions of the conservative pundit he portrayed for nine years on Comedy Central's The Colbert Report. Yes, Colbert is thriving as himself, but one area where Colbert and “Colbert” equally shine is their musical talent. With the inaugural episode opening with Stephen singing the national anthem in different locations around the country, and closing with a star-studded rendition of “Everyday People” lead by Mavis Staples, it's a promising indication that Colbert's new Late Show is going to have a strong musical element. It's in toe-tapping anticipation of these great moments still to come that we look back on Stephen Colbert's Top 5 Musical Moments.


5) Colbert Interviews Nas (2008)
Colbert's had plenty of outstanding interviews with musicians over his almost two straight decades on the air, but in retrospect, his most impressive might have been his summer 2008 interview with rapper Nas. A notoriously challenging artists to speak to, few have really been able to engage Nas in a dialogue with the same depth he brings to his lyrics. Here, Colbert weaves his magic to both get Nas to respond directly to some of his harshest criticisms, especially in wake of promoting his Untitled album after it's unceremonious name-change, while simultaneously sending up hip-hop's biggest critics' accusations of what the genre's effect on society truly is. It's nothing short of masterful.

4) Stephen and the Colberts – “Charlene” (2006)
For The Colbert Report's first Valentine's Day show, Stephen dusted off his former '80s band Stephen and the Colberts' single “Charlene.” Prefacing it with the note that his band did mostly “love songs and power ballads,” “Charlene” captures the best elements of both. But it's in Colbert's perfect '80s dance maneuvers that really bring the video to life.

3) Alicia Keys and Stephen Colbert – “New York State of Mind Part 2 1/2” (2009)
When Alicia Keys guested on The Colbert Report in 2009 at the apex of “Empire State of Mind's” popularity, it was a given she was going to perform her solo version of the song on the show. What wasn't expected was Colbert joining in for his take on what he believes New York to be (roughly eight blocks in Times Square) with the level of MC mic mastery that would even make Jay-Z proud.

2) Stephen Colbert vs. The Decemberists (2006)
Ending The Colbert Report's first year was a fun-spirited feud between Stephen Colbert and The Decemberists. After accusing the band of stealing the idea for his green screen challenge, the group upped the ante by challenge Colbert to a guitar shred-off. In probably the best rock contest ever judged by Henry Kissinger and boasting an incredible Peter Frampton cameo, it became among the first of many iconic Colbert Report moments.

1) “We'll Meet Again” and We Did! (2014)
Few things captured the importance of Stephen Colbert and The Colbert Report's impact like the show's star-studded closing number. In a possible nod to the closing of Stanley Kubrick's Dr. Strangelove, or perhaps just a face value sincere final sendoff, Colbert and one of the most diverse line-up of intellectuals and celebrities ever assembled performed a rendition of the song made famous by Dame Vera Lynn 75 years prior. Perhaps 3/4 of a century from now, this version will be looked back upon as one of the song's most memorable performances.

See also:
The 50 Best Things About the OC Music Scene
The 50 Worst Things About the OC Music Scene
The 25 Greatest OC Bands of All Time: The Complete List

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