 by Julian Spivey
The last few weeks of the “Late Show with David Letterman” produced some of the greatest, funniest and most tear-inducing moments in that show’s legendary history. Here’s a rundown of the 25 best moments from the show’s last couple of months on the air ... 1. Dave Signs Off David Letterman signing off for the very last time on late night television was bound to be the top spot on this list all along. It was a moment full of grace and class as the legendary comedian/broadcaster thanked his crew, his audience and most importantly his wife Regina and son Harry. He then signed off with the simple, yet eloquent: “The only thing I have left to do, for the last time on a television program, thank you and goodnight.” 2. Foo Fighters/Best Of Montage The very final thing to ever appear on the “Late Show with David Letterman” was a performance of Dave’s favorite band the Foo Fighters performing his favorite song “Everlong.” Letterman has mentioned multiple times on the show why this song and band is so important to him and he did it once again on Wednesday night (May 20) when he explained how the Foo Fighters had canceled a tour in South America just to play this song for him on the episode in 2000 when he returned from open heart surgery. The Foos played an epic version of “Everlong” as the show was sent off air by an amazing montage of the greatest clips of guests and moments in the show’s wonderful history. 3. Norm Macdonald’s Stand-Up Norm Macdonald’s final stand-up routine on Friday, May 15 was the very last stand-up routine performed on the “Late Show with David Letterman” and certainly one of the most memorable. Letterman has always enjoyed Macdonald’s brand of sarcastic, witty humor that frequently mirrors his own. Macdonald was as funny as ever during the set, but it’s really how emotional he got telling Letterman how much he meant to him that just made this a classic moment. Macdonald broke down in tears while telling his favorite Letterman joke, one that he claims is his favorite joke of all-time. 4. Jack Hanna’s Farewell For my money zoologist Jack Hanna is the greatest guest of all-time on David Letterman’s late night programs thanks to the camaraderie the two men have together and the hilarity that always ensued through Letterman’s interactions with Hanna’s many great animal guests over the years. The farewell appearance for Hanna, who appeared on Letterman’s shows more than 100 times, included a fantastic montage of his greatest moments on the show that teared the long-time guest up. 5. Final Top 10 David Letterman has had some huge names come out to read his nightly Top 10 lists in the past, but no Top 10 has ever been as star-studded as his very last one on Wednesday, May 20 when 10 of his favorite recurring guests walked out onto the Ed Sullivan Theater stage to announce 10 Things I Have Always Wanted to Say to Dave. The celebrities included Alec Baldwin, Barbara Walters, Steve Martin, Jerry Seinfeld, Jim Carrey, Chris Rock, Julia Louis-Dreyfus, Peyton Manning, Tina Fey and Bill Murray and the final Top 10 turned out to be one of the funniest and most memorable of all-time. 6. George Clooney Handcuffs Over the last two months of the “Late Show with David Letterman” many celebrities have remarked that Letterman was making a huge mistake in his decision to retire and how much they loved him and didn’t want him to go. Oscar-winner George Clooney took this one step further when he came out for his final appearance of the show on Thursday, May 14 and he handcuffed himself to Letterman. Clooney remained handcuffed to Letterman for the remainder of the episode through his entire interview, an interview with musician Tom Waits (in which Clooney had to awkwardly proportion himself on a stool between the two and Waits’ musical performance. Taking the gag one step further Clooney returned the next night still handcuffed to Letterman and the two were finally freed by Paul Shaffer and some wire cutters. 7. Michael Keaton Embarrasses Dave Over the years Oscar-nominated actor Michael Keaton has been one of the very best guests on the “Late Show with David Letterman” because he and Letterman are longtime friends that have a great rapport with each other. The two became friends in their stand-up comedy days in the late ‘70s, which included a guest spot on a Mary Tyler Moore television special in which the two had to sing and dance. Letterman is obviously not the type of guy you’d ever have expected to participate in such an event and thus Keaton thoroughly embarrasses him to the point of hiding under his desk when he shows the clip of the two of them from the late ‘70s special. 8. Norm Macdonald Last Interview Late night television has turned into more of a medium of “what can we get people to watch us doing on YouTube or Hulu tomorrow?” Thus a great and crucial part of the medium – the actual interviews – have taken somewhat of a step back (particularly when it comes to Jimmy Fallon’s massively popular “The Tonight Show”). Well, in his last appearance as an interviewed guest back in March Norm Macdonald showed the world exactly what a late night talk show should be when he thrilled and cracked up his comic hero David Letterman with terrifically hilarious life stories. You can read more about that appearance: HERE 9. Adam Sandler Tribute The funniest thing about Adam Sandler’s career has always been his musical comedy and this dates back to his earliest days on “Saturday Night Live.” So it was no surprise when Sandler’s tribute to Dave was a musical one, as many of the tributes to Letterman on the ‘Late Show’ over his last few weeks proved to be. Of all of these memorable musical tributes Sandler’s was the funniest and also the most emotional with the funny man tearing up toward the end of his performance. It was amazing just how many comedians both on the ‘Late Show’ and those hosting their own late night shows (Jimmy Kimmel, Jimmy Fallon) got teary-eyed in tribute to Letterman. That just goes to show his legacy and the impact he’s had on others. 10. Jerry Seinfeld’s Stand-Up The great thing about Jerry Seinfeld is that every time to this day, even as a celebrity worth $900 million, that he appears on any late night talk show he will perform a stand-up set before being interviewed. This was no different during his final appearance on the “Late Show with David Letterman,” but what was different about his final appearance was the stand-up set itself. Almost nobody in the audience both in the studio or watching on television knew this at the time until Seinfeld was being interviewed by Letterman afterward, but the entire set was the very first one that Seinfeld had ever performed on Letterman’s ‘Late Night’ all the way back on his very first appearance in 1982. Letterman said that it took him until about halfway through Seinfeld’s set before he realized this. It was a truly special tribute from Seinfeld and proof of just how well his comedy stands up over 30-plus years. 11. Jason Isbell’s Warren Zevon Tribute Perhaps David Letterman’s all-time favorite musical guest was the vastly underrated Warren Zevon, who memorably had an entire episode dedicated to him and his music in 2002 when it was announced that he had incurable cancer and would soon die. One of Letterman’s favorite guests of recent years has been critically-acclaimed Americana singer-songwriter Jason Isbell who brilliantly, along with his wife/musician Amanda Shires, paid tribute to Zevon with their cover of his “Mutineer,” which he himself had performed on his last Letterman appearance. It was a brilliant cover that truly left Letterman a bit misty-eyed. You can read more about that performance: HERE 12. Tracy Chapman Sings “Stand By Me”/First Aid Kit “America” Many of the greatest moments over the last couple of months of the “Late Show with David Letterman” were musical moments, almost all of them seemingly hand-picked or requested by Letterman or band leader Paul Shaffer. Two of the ones that particularly stand out are songs that Letterman said he would sing to his son Harry when he was younger. Ben E. King’s standard “Stand By Me” and Simon & Garfunkel’s great “America.” “Stand By Me” was breathtakingly performed by Tracy Chapman on the show just a couple of weeks before King would pass away. Americana/Folk duo First Aid Kit would thrill Letterman’s audience with their beautiful take on “America.” 13. Julia Roberts Kiss Throughout the years Julia Roberts has obviously been one of David Letterman’s very favorite guests and the two have mutually flirted with each other on the air throughout their entire television friendship, usually culminating with Roberts wanting to kiss Letterman. Roberts has gone on record as saying she was thoroughly frightened the very first time she went on Letterman because she had seen the way he eviscerated other celebrities on the show whom he might not have cared for. Letterman, however, took a liking to Roberts right away and the bond never swayed. Roberts and Letterman memorably shared one final kiss on her last appearance in early May. 14. Behind the Scenes One of the truly great things about David Letterman’s farewell episode of the ‘Late Show’ on Wednesday, May 20 was the behind the scenes segment that showed fans of the show exactly what Dave does before the tapings each day. The segment showed Letterman arriving to the studio incredibly early in the morning, just to typically catch a few more hours of sleep in his office, as well as joking around with staff members and then trying to compile jokes and segments for the nightly episode. 15. Ray Romano’s Gratefulness Toward Letterman Without David Letterman there would be no Ray Romano and Romano knows this as a fact and told Letterman so on his final appearance on the show in early May. Romano was a struggling stand-up comedian in the early-to-mid ‘90s who went on Letterman to do a set and immediately captured the iconic comedian’s interest. We’ve all heard stories of how doing well on “The Tonight Show with Johnny Carson” could make or break a young comedian’s career as it had made Dave’s when Carson liked his act so much. Letterman repaid the favor with Romano whom he’d contacted shortly after his appearance on the ‘Late Show’ and said he’d like to make a sitcom based on his comedy for his Worldwide Pants company. That show would become “Everybody Loves Raymond,” one of the most successful sitcoms of all-time. Romano’s teary-eyed thanks to Letterman was a true highlight, even though Letterman humbly (and wrongly) claimed he had nothing to do with Romano’s success. 16. Martin Short Tribute Martin Short has been no stranger to performing musical tributes to David Letterman over the years on the ‘Late Show,’ but his farewell musical moment to him will likely be remembered as the very best, even though it’s one the comedian said he never expected to perform until Letterman’s funeral. This nearly five-minute performance proves that Martin Short is the king of musical tributes. If the Tony Awards are looking for a future host he should be their first phone call. 17. Billy Crystal’s Tribute Musical tributes to David Letterman were plentiful over the final weeks of his show with ones being done by Martin Short, Adam Sandler, Nathan Lane and Billy Crystal. Crystal’s musical performance included the hilarious lines: “You survived shingles and a bypass/Proving you actually had a heart” and “it’s true Cher called you an ***hole, but you’re the ***hole we love.” 18. Howard Stern Tries to Kiss Dave Howard Stern has been another one of David Letterman’s favorite recurring guests on his broadcasts for nearly 30 years and the two seem to have a warm feeling for each other. Letterman is famously not emotional or even one for emotion, so things got incredibly funny when Stern asked Letterman for a hug – which the comedian initially wanted no part of before finally relenting. Things got even funnier when Letterman finally went in for the hug and Stern attempted to kiss him with Letterman trying his best to squirm away. 19. Eddie Vedder’s “Better Man” Eddie Vedder’s performance of the Pearl Jam classic “Better Man” on the final week of David Letterman’s shows on Monday, May 18th will no doubt go down as one of the very best and most memorable performances ever to appear on the “Late Show with David Letterman.” Vedder gave one of the most high-energy performances ever on the show just playing solo with Paul Shaffer and the CBS Orchestra brilliantly backing him up. Pardon the corniness, but there will never be a better man on late night television than David Letterman. 20. Steve Martin & Guests “Will The Circle Be Unbroken” During Steve Martin’s final appearance on the “Late Show with David Letterman” the two old friends spent a lot of time playing off of each other as they so brilliantly have for 30-plus years with Martin acting half of the time like he didn’t actually care much for Letterman. Letterman than re-aired a fantastically funny segment the two shot in the late ‘90s called “Steve & Dave’s Gay Vacation” where the two comedians fall in love with each other. The real highlight of Martin’s final visit was seeing him, a Grammy-winning banjo player, perform the traditional country music standard “Will the Circle Be Unbroken?” with the incredibly talented Rodney Crowell, Emmylou Harris and Amos Lee. 21. Bob Dylan’s “The Night We Called It a Day” Bob Dylan is not one to perform on late night television talk shows very often. That made his appearance on David Letterman’s final week of shows this week quite the big get for that show. Dylan had performed on Letterman’s programs a couple of times before, but Tuesday (May 19) was his first in 20-plus years. Dylan, who frankly didn’t necessarily appear to have wanted to be there (but does the prickly performer ever?), performed the fitting Frank Sinatra standard “The Night We Called It a Day.” Before the appearance Letterman announced that there were two things he always wanted his son Harry to know: 1) treat everybody you meet with kindness 2) Bob Dylan is the greatest American songwriter ever. 22. Bill Murray Bursts Out of Cake Bill Murray has a great history of incredibly outrageous performances on David Letterman’s programs over the last 30-plus years. Murray has memorably been Letterman’s first guest both on ‘Late Night’ on NBC in 1982 and on the ‘Late Show’ on CBS in 1993. On Tuesday, May 19 Murray also became Letterman’s very last guest and made his entrance by popping out of a huge cake and subsequently embracing Letterman and getting cake remnants all over the departing host. Just another outlandish entry from a man full of them over the years. 23. Reminiscing with Tom Dreesen Tom Dreesen may not be a household name to many, but this stand-up comedian who famously spent much of his career opening for the legendary Frank Sinatra has been a friend of David Letterman’s for a very long time since they were up-and-coming stand-ups in the ‘70s. Dreesen always thrills the audience with stories of his time working with Sinatra, but on his final appearance he regaled the audience with lovely stories of his time spent with Letterman on the comedy club circuit back in the days of old. 24. “Not Getting The Tonight Show” It’s not easy to remember monologue jokes, even if they made you almost split your side open from laughing so hard, but David Letterman made a joke toward the beginning of his last ever monologue on Wednesday, May 20 that is absolutely priceless and will be hard to ever forget. Letterman came out and said to his audience: “I’ve got to be honest with you, it’s beginning to look like I’m not going to get ‘The Tonight Show.’ It was the perfect sendoff to the decade’s old story of how Letterman was screwed out of hosting “The Tonight Show” in the early ‘90s even though he always seemed like the legendary Johnny Carson’s hand-picked and rightful replacement. 25. Paul Shaffer Interview Paul Shaffer has always been such an integral part of David Letterman’s programs over the last 30-plus years as the show’s band leader. It’s because of Shaffer that the show has always been the best one on late night television when it comes to fantastic musical moments. However, Shaffer has only had the opportunity a few times over the years to be interviewed by Letterman and his boss made sure to get him some airtime in the show’s last couple of weeks. Shaffer told stories of his favorite musical moments on the show, like the time he met Bob Dylan backstage, before debuting a special music video of “On Broadway.” What was your favorite moment from David Letterman’s last couple of months on the air?
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