 by Julian Spivey
After more than 30 years on late night television David Letterman is retiring after his final show on Wednesday, May 20. The legendary comedian who has inspired nearly all of the comedians you see hosting shows on late night TV today has had some truly entertaining recurring guests throughout his long tenure in late night. It’s truly a hard task to compile a list of his 10 greatest guests and some really memorable ones like Bruce Willis, Julia Roberts, Will Smith, Tina Fey and Michael Keaton failed to make this list. One reason Letterman will truly be missed is his interviews with celebrities, especially those you could tell he really respected and admired made his show more interesting and entertaining than any other show on late night. No other current late night host seems to have the same rapport with their guests and that’s one reason to be worried about the format come the end of Wednesday night’s farewell. 10. Joaquin Phoenix Joaquin Phoenix is not a better all-time guest than Julia Roberts, Bruce Willis or Will Smith per se. He’s appeared on Letterman’s ‘Late Show’ far fewer times than those legends, but his appearance on the ‘Late Show’ on Feb. 11, 2009 was so memorable that he couldn’t be left off of this list. Letterman’s interview with Phoenix was the greatest single interview I’ve ever seen on the ‘Late Show,’ and even though we all know now that it was an act on Phoenix’s part for a mockumentary he was filming with fellow actor Casey Affleck it is still fantastic because Letterman didn’t know at the time it was an act and treated Phoenix accordingly. Letterman’s bite has rarely been as effective as it was during this interview as he completely obliterates Phoenix for his unusual behavior. 9. Norm Macdonald Norm Macdonald was built for late night television appearances. The extremely hilarious and personable late night guest clearly admires Letterman and has frequently reminded him, especially in his previous appearance on March 18, that he’s his comedic hero. Macdonald even impersonated Letterman on “Saturday Night Live.” What makes Macdonald such a fascinating guest on the ‘Late Show’ is that he generally can crack Letterman up unlike no other comedian I’ve ever seen on his show and his hilarious long-form jokes and stories show exactly what a late night talk show was meant to be. Macdonald’s most epic guest appearance on the ‘Late Show’ came when he announced he was fired from ‘SNL’ on Jan. 7, 1998. 8. Warren Zevon David Letterman has had just about every big star you can possibly think of as a musical guest during his 30-plus year tenure on late night television, but the one musical guest that he was perhaps closest to was the underrated and often unheard of Warren Zevon. Zevon appeared on Letterman’s ‘Late Night’ and ‘Late Show’ numerous times between 1982 and his death in 2003. His final appearance on the show was extremely memorable and touching as Letterman dedicated the entire episode to Zevon as not just the musical guest, but his lone interview as well. During the 2002 episode Zevon performed multiple songs, including a request from Letterman to do “Roland the Headless Thompson Gunner,” which would become his final public performance. 7. Robin Williams The late, great Robin Williams would most likely appear on the top 10 greatest guests list of any late night television show that’s aired over the last two-plus decades. The incredibly talented and wild improvisationalist was pretty much out of control with hilarity every time he stepped on a late night stage, but especially during his many appearances on David Letterman’s programs. It was never really an interview, just Letterman kicking back at his desk and enjoying Williams’ little one-man show for 15 minutes. After Williams’ tragic death from suicide in 2014 Letterman gave a memorable teary-eyed tribute to the comic legend, whom he’d met as a stand-up before either of them had even hit it big. 6. Andy Kaufman Speaking of wild comedians on David Letterman’s programs there was none wilder than the late Andy Kaufman who made many a memorable appearance on Letterman’s early years on ‘Late Night’ on NBC with his charades and gags. Kaufman appeared on ‘Late Night’ an incredible 11 times in just a two-year span from 1982-1983 and even appeared on Letterman’s “The David Letterman Show” morning show in 1980 multiple times. His most famous, or infamous if you’d rather, appearance on ‘Late Night’ came in 1982 when his mock wrestling feud with pro wrestler Jerry Lawler came to a head when Lawler slapped Kaufman across the face and sent Kaufman on a profane and naturally censored for television tirade in the studio. The incident was memorably recreated for the Andy Kaufman biopic “Man on the Moon,” starring Jim Carrey in 1999 with Letterman and Lawler portraying themselves. 5. Steve Martin Steve Martin has always been an incredibly fun guest on David Letterman’s programs with his sarcastic style of humor playing off of Letterman’s very well. You could always tell that these two comedic giants had a great respect and liking for one another and the comradery between the two has always been incredibly fun to watch, especially when Martin has acted over the years like he doesn’t like Letterman at all. The best ‘Late Show’ bit between Letterman and Martin came in the form of the hilarious 1998 segment ‘Steve and Dave’s Gay Vacation.’ 4. Tom Hanks Tom Hanks is likely the greatest actor in cinema of the last three decades, but has spent the bulk of his film career in very dramatic roles. But, Hanks is a generally funny guy and seemingly one of the most personable celebrities in Hollywood and this has always come out in his extremely entertaining guest spots on Letterman’s ‘Late Show.’ Hanks always showed up to the ‘Late Show’ with a bevy of fantastically hilarious stories from his daily life that always managed to crack up both Letterman and his audience both at the Ed Sullivan Theatre and those watching at home. Hanks is a great late night guest no matter what talk show he appears on, but he always had such a great rapport with Letterman that it feels like his best late show TV appearances are bound to be behind him. 3. Bill Murray Bill Murray has been a monumental guest for David Letterman all the way through Letterman’s late night career. Murray was Letterman’s very first late night guest on ‘Late Night’ over on NBC in 1982. On that episode Murray told Letterman, “You got out of Indianapolis and didn’t look back. I’m just waiting for the other shoe to fall on you, man, and I want to be there when it hits the floor! I had a chance to strangle Richard Nixon and I didn’t – and I regret it!” Murray was also Letterman’s first guest on ‘Late Show’ in 1993. Murray has always been a fascinatingly entertaining guest as he usually comes out in a wild outfit or does some sort of musical bit in honor of Letterman. It was recently announced that Murray will fittingly be Letterman’s final guest on the ‘Late Show,’ although his appearance is the night before Letterman’s finale. Any guests, if the show chooses to have any, for the finale have yet to be announced. 2. Jay Thomas Jay Thomas is very likely the least famous person on this list, but he’s easily been one of the greatest guests on Letterman’s ‘Late Show.’ Thomas has two great traditions on the ‘Late Show’ annual Christmas episode that date back to 1998. His traditions include throwing a football with Letterman at the giant meatball that sits atop the Christmas tree on the ‘Late Show’ stage and telling a story that Letterman has deemed “the greatest late night story of all-time.” The football throw started in 1998 when then New York Jets quarterback Vinny Testaverde was on the show and trying to knock the meatball down. Thomas, in the green room as the next guest, grew irritated that a professional QB couldn’t hit a meatball off a tree and ran out to the stage, grabbed a ball and immediately knocked the meatball off. Letterman has invited him back every year since (except for 2013 when Thomas had surgery) to join in the tradition. The “greatest late night story of all-time” is the incredibly funny story of Thomas’ younger days as a local DJ and having to do a gig with Clayton Moore, the actor who portrayed TV’s Lone Ranger, and getting into a road rage incident with the Lone Ranger in his backseat. As long as late night television continues there will never be a greater story told on a talk show. 1. Jack Hanna Jack Hanna has appeared on David Letterman’s talk shows more than 100 times over the last three decades. Only Regis Philbin and Marv Albert have appeared on more episodes during Letterman’s legendary run. The award-winning zookeeper and animal expert has brought many exotic and fascinating animals to Letterman’s stage over the years and Letterman’s reactions and interactions with both the animals and Hanna has proven to elicit perhaps more laughs than any of these other nine guests on this list combined. Every time you saw that Jack Hanna was scheduled to be on ‘Late Night’ or ‘Late Show’ you knew it would be must-see TV. Hanna’s final appearance on the ‘Late Show’ on April 29th was a highly emotional one for the legendary zookeeper who was brought to tears when the show did a terrific montage of his appearances on the show over the last three decades. Who do you think was Letterman’s greatest guest of all-time?
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