Published on May 19th, 2015 | by Andy Sedlak

10 Best Music Moments From Letterman’s Final Episodes

We can only hope Stephen Colbert has the ear that David Letterman did.

It looks good so far. Randy Newman, Yo-Yo Ma, Jeff Tweedy, Willie Nelson, Michael Stipe and Pussy Riot all made appearances in The Colbert Report finale. But Letterman broke acts.

You know the vast ocean of fan boys and gals who have seemingly dedicated their entire existence to adoring the Dave Matthews Band? Well, the world got its first taste of DMB when the band performed “What Would You Say” on The Late Show in February 1995. It was the band’s national television debut. Furthermore, R.E.M., Hootie and the Blowfish, Oasis, Future Islands and Amy Winehouse all made their network TV debuts with Letterman. Hell, the guy reunited Sonny and Cher. His place in musical history is in cement.

I always felt that so many of Letterman’s musical guests took on the personality of the show, which itself was a safe zone for eclectic goofballs, experimental youngsters and vets with gas left in the tank.  Dave and his crew were inviting to artists.

After 33 years of music on Letterman, you might be tempted to think you’ve seen it all. Not true. Letterman’s final run has given us once-in-a-lifetime performances from some of Dave’s favorites. John Mayer performing “American Pie?” Tracy Chapman singing “Stand By Me?” It’s whatever Dave wants at this point.

We’re all busy, so maybe you didn’t catch these gems the first time around. If not, enjoy. It sure seemed like Dave did.

Oh, and get to work, Colbert.

#10 – John Mayer performs “American Pie”

Wearing a blue and yellow Late Night varsity jacket, John Mayer and Paul Shaffer’s CBS orchestra tackled the immaculate monster that is “American Pie.” Their performance times out to about nine minutes. Although Mayer garbles the “It landed foul on the grass” line, we’re reminded that it’s that kind of charming roughness that was always the backbone of The Late Show. Don McLean, who is now 69 years old, was surely proud.

#9 – John Mellencamp performs “Longest Days”

Shirking his cue to start the song, Mellencamp begins his performance by telling a story about his ailing grandmother and relays advice she once gave him to a TV host counting his days. “Life is short, Dave, even in its longest days … so enjoy yourself.” The old cynic could hardly hold back his tears.

#8 – Future Islands perform “The Chase”

Quite possibly the last band Letterman will get credit for breaking. Their first performance of “Seasons (Waiting on You)” went viral in 2014, mostly thanks to frontman Samuel Herring’s he-can’t-be-serious dance moves. The delight though, is that Herring is serious. He dedicates this performance of “The Chase,” to the band’s hometown of Baltimore, reeling at the time from riots. My wife likes to say that when you really love a song, you’ll know it after hearing the first line. This one starts, “I take my licks like a man…”

#7 – Jason Isbell and Amanda Shires perform “Mutineer”

The husband-and-wife combo tackles the Warren Zevon classic, “Mutineer.” Letterman fans are well aware of Zevon’s history with the show. He used to fill in for Paul Shaffer from time to time and Dave himself was a monster fan. Zevon was diagnosed with terminal cancer in 2003, and Letterman invited him on to be his only guest that October. YouTube those interviews – they’re unbelievable. Before Zevon died, he said Dave was the “best friend” his music ever had.

#6 – The Dave Matthews Band performs “What Would You Say”

As stated above, DMB made its television debut with this song in 1995. They were invited to revive it during Dave’s final run. The host, clearly besotted at the end of the song, asked the band to play another. They did so happily as the credits rolled. No “goodnight” from the host. Just music.

#5 – Adam Sandler performs an Ode to Dave Letterman

We’ll count this because it’s the funniest thing Sandler has done in 15 years. Halfway through it turns into a real, honest-to-God tribute.

#4 – Ryan Adams performs “Starting to Hurt”

Adams revisits an old friend specifically for Dave. The performance was without frills – it’s straight up rock & roll. It’s also as crisp as crisp can be. When it’s over, Letterman asks Adams to play it again. He does so immediately.

#3 – Paul Shaffer’s “On Broadway” music video

Shaffer’s granted room to indulge a bit, and comes up with a music video for “On Broadway.” Martin Short, Lorne Michaels and Darlene Love make cameo appearances. Everyone clearly had a ball paying tribute to not only The Drifters and the old Brill Building songwriting combos, but to where Shaffer and Letterman have worked since 1993. When the video ended, Letterman’s longtime sidekick was wiping away tears.

#2 – Tracy Chapman performs “Stand By Me”

Another special request from the host. Letterman introduces Chapman by saying he used to sing this song to his son to help him nod off at night. Chapman’s spare arrangement is beautiful, and one can only hope Ben E. King was watching somewhere that night. King would pass away 13 days later.

#1 – Tom Waits performs “Take One Last Look”

Waits unveils a brand new song for his final Letterman performance. The poignantly titled “Take One Last Look” was a gentle directive to not only the host, but to the legions of fans still coming to terms with Letterman’s departure.

Bonus performance: Will Lee, the CBS Orchestra and Jimmy Webb perform “MacArthur Park”

And for the hell of it, I want to include my favorite musical moment ever on Letterman. It’s primarily handled by Will Lee, who is the bass player in the CBS Orchestra. A few years ago, Letterman gave him the go ahead to perform a rendition of “MacArthur Park,” the old Jimmy Webb song that Donna Summer later turned into a hit. Never one to lay off the indulgence, Shaffer enlisted Webb to come back and play keys. It didn’t stop there, however. A string section, a giant cake prop and solos galore, it became a showpiece for the entire CBS Orchestra. And Lee, who has been with Letterman and Shaffer since Day One, clearly reveled in his opportunity to shine. I’ll never get tired of watching it.

Letterman’s final episode of The Late Show airs Wednesday night on CBS.

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About the Author

Andy Sedlak is a former television reporter who lives in Dayton, OH. He grew up in a household that pumped Bruce Springsteen and Billy Joel every weekend. He instantly became a new man when he discovered Bob Dylan’s “Like A Rolling Stone” in junior high.

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