I'd been thinking about David Letterman lately anyway, so in the wake of his retirement announcement, it seems as good a time as any to run down his top ten guests from over the years. Most "Best of Letterman" lists will feature such infamous guests as Farrah Fawcett, Crispin Glover, and Joaquin Phoenix, but while those interviews are rightly legendary as novelties, that's not the focus of this list. Rather, these are the people who, when announced to be on the show, could always be counted on to bring out the best in Letterman's sensibilities as host and as entertainer.
10. Julia Roberts
There seems to be an inverse relationship between how glamorous a star is and how interested in them Letterman seems to be, but for whatever reasons, Julia Roberts is the exception. She's one of the biggest stars in the world, and he's one of its biggest cranks, yet their segments together are always warm and cozy. The palpable mutual respect and affection between them is all the more endearing because of how uncommon it is among the pantheon of prolific guests.
9. Howard Stern
Letterman was one of the few mainstream hosts who treated the shock jock as a legitimate interviewer, perhaps because they're kindred spirits in their lack of regard for status and airs. They both up their game when they're together, and it shows.
8. Harvey Pekar
You gotta go back to Late Night on NBC for the comic writer/artist Pekar's segments (dramatized in the biopic American Splendor), but they're amazing. Letterman's entire shtick has always been that he's unimpressed by pretty much everything...and Pekar was the repeat guest who was entirely unimpressed by being a guest on Letterman's show. It's like watching a game of apathy chicken between two kamikaze pilots.
7. Oprah Winfrey
The "feud" between Letterman and Oprah was the stuff of entertainment legend, and so when the daytime TV queen finally appeared on the late night TV king's show in 2005, there was a sense of historical triumph. Yet, as sometimes happens, the buildup was more satisfying than the payoff. Their interview on her show was more rewarding - particularly their audience-free post-show one-on-one - but not as entertaining as the running joke of the feud itself.
6. Jack Hanna
Critters are always funny, even when they're lethargic and sedentary. Johnny Carson understood the comedic value of having exotic animals on a late night variety show, and so does Letterman. These are the segments where Letterman's quick wit and presence of mind shine.
5. Gene Siskel and Roger Ebert
The famed critic duo was not only a lot of fun to watch on their own, but they triangulated with Dave with no one pulling any punches. Fun fact: Siskel and Ebert are the reason that there are two guest chairs on Letterman's set.
Madonna was one of the very first guests on Late Show, and boy did she make a splash! She was inflammatory and vulgar, and reportedly banned from the show. Of course, she was also the guest that had us all talking for quite awhile. I remember vividly Madonna sharing that urinating on your foot in the shower is an effective treatment for athlete's foot. We were all captivated by Letterman squirming in his seat. She made nice and got to come back, and each time it was gold.
3. Dorothy Mengering (Dave's Mom)
I don't think Dave's Mom was ever a guest proper, but she's been a recurring guest by phone and video over the years, and has appeared in-studio on occasion. She looms large as part of Letterman's public persona as the one guest who has the most power to embarrass him, and the one he has the least power to treat with his full snark. Plus, she's a great sport and brings the funny all on her own.
2. Regis Philbin
Regis's hyperactivity makes him an easy target for Letterman, and his genuine enthusiasm has somehow made him impervious to the host's barbs. It can be hard to tell at times whether Regis doesn't really get being the butt of a joke, or whether he's some kind of meta-level master of counter-trolling. Make no mistake, though, of the high regard in which they hold one another: When Dave returned from his angioplasty, Regis was one of his substitute hosts and his first guest upon his return.
1. Richard Simmons
Richard Simmons has all the energy of Regis, but none of his deflective skill. No one was ever an easier target for Letterman's needling, but no one could put Letterman in the hot seat quite the way he could, either. An infamous prank with a fire extinguisher led to a six year rift between the two, and wouldn't you know that when Simmons finally acquiesced and returned, Dave was there with yet another prank.