David Letterman's 11 Best Regular Guests

Bill Murray and Bob Dylan will be the last two guests to appear on a David Letterman talk show when they stop by the Ed Sullivan Theater tonight. Letterman’s last episode is tomorrow, but no guests have been announced. Murray is the perfect final guest—he was the first guest on NBC’s Late Night with David Letterman and CBS’s The Late Show with David Letterman, and was even the first guest on Letterman’s short-lived morning talk show on NBC in 1980.

Murray was one of many guests who appeared regularly on Letterman’s shows throughout the years. If you’ve been watching the show wind down over the last few months you’ve seen most of these guests give teary farewells after watching decades-spanning clips of their various appearances. It’s been a sad but wonderful goodbye tour, and before it winds down let’s look back at the best recurring guests throughout Letterman’s career.

11. Charles Grodin

Grodin’s aggressive appearances on Letterman weren’t unique. He’s been an infamously confrontational talk show guest for his entire career. It took a fellow grouch to help Grodin reach the next level, though, and he found his perfect foil in Letterman. Letterman embraced Grodin’s performance art, and the two sometimes planned bits in advance together. During the great NBC episode where Dave broadcasts from his house while waiting for the cable guy, Grodin shows up at an empty studio and is interviewed over a monitor. Grodin’s put-on persona was waiting for a show like Letterman’s.

10. Andy Kaufman

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Kaufman died only a few years into Letterman’s tenure, but he was a vital early guest in terms of establishing Letterman’s comedy bona fides. Already famous from Taxi and his Saturday Night Live appearances, Kaufman was America’s preeminent weirdo when Late Night debuted in 1982. Some of Kaufman’s best remembered bits happened on Late Night, from introducing Dave to his adopted family, to his kayfabe brawl with Jerry “the King” Lawler. By letting Kaufman do almost whatever wanted, Letterman fostered a sense of danger that hadn’t been seen on a network talk show before.

9. Harvey Pekar

For decades Harvey Pekar wrote a great comic book called American Splendor. You’ve probably seen the movie of the same name, starring Paul Giamatti as Pekar. Pekar was a crusty blue collar guy from Cleveland who wouldn’t let people box him into preconceived notions of what a crusty blue collar guy from Cleveland should be like. He was a perceptive critic of not just the jazz music he loved but culture in general. His outspoken nature and unusual combination of blue collar and bohemian made him a great guest on Letterman. He appeared eight times over two years in the 1980s, and was one of the few guests who could give it back to Dave when Dave was sarcastic or condescending. Like Grodin, Pekar could be confrontational, but it didn’t feel like a performance—it felt like two surly guys griping at each other. Although Letterman was a glib, polished TV comedian, though, Pekar was an earnest and honest citizen. Their relationship came to an abrupt and awkward end when Pekar attacked NBC’s owner GE during an appearance, calling Dave a shill for defending them. He did make a later appearance on the Late Show after Letterman moved to CBS, and the old crusty magic was still there.

8. Regis Philbin

Philbin made more guest appearances on Letterman’s shows than anybody else. Dave’s show gleefully pushed the envelope of what you could expect from TV comedy, but beneath the irony he always maintained a genuine appreciation for classic television. Philbin is a direct connection to the earliest days of television, but he’s also a high-strung weirdo who fits in well with Letterman’s irreverence.

7. Howard Stern

You don’t have to like Stern’s shock jock antics to recognize that he and Dave have a deep respect for each other. Their style of humor might be different, but they both have strong, idiosyncratic personalities that thoroughly define their shows. They’re also both not afraid to needle or confront their guests, or to be openly hostile towards their advertisers or corporate owners.

6. Teri Garr

Garr was one of the most frequent guests on Letterman’s NBC show, dropping by over 30 times in 11 years. They had amazing chemistry with one another—instead of the canned and publicist-approved interviews you often see on talk shows, they seemed to have legitimate conversations, almost as if there wasn’t an audience watching in. Garr was also willing to go along with whatever weirdness Letterman and his writers planned for her, including one episode where Dave talked her into taking a shower on the show. Her appearances slowed down as she battled with health issues, but she’s made occasional appearances on Dave’s CBS show.

5. Jack Hanna

Dave wasn’t the first talk show host to fool around with zoo animals, but the almost quarterly visits from the Columbus Zoo and Aquarium’s Jack Hanna have been a highlight throughout Dave’s entire career. Sure, the animals are cute and Dave plays off them brilliantly, but the true draw was the relationship between Letterman and Hanna. Dave clearly found a compatible comedy partner in Hanna, who combined a deadpan delivery and surprisingly quick wit with an excitable energy that would regularly break through his attempts at stoicism.

4. Bruce Willis

Before Bruce Willis became a huge action star, he was primarily thought of as a comedic actor. He starred on the breakout primetime hit Moonlighting, which could be seen as one of the first network shows to try and work in the same meta and irreverent tone as Dave’s talk show. Willis can still be hilarious, and his main outlet for that for the last few decades has been Late Night and Late Show. Here’s a great compilation of some of his best hits.

3. Julia Roberts

The other night my wife called Dave “weirdly sexy.” That side of him rarely came out on TV, but was usually front and center whenever he and Julia Roberts flirted their way through another adorable interview. (Between Roberts and my wife, maybe Dave has some kind of weird sway over women from Georgia?) Roberts has been on Dave’s show about once a year since her first appearance in 1988, and every interview almost felt like a first date. They have amazing chemistry together, and her appearances were always a treat. She swung by the show for the last time last week, and like so much of Dave’s farewell tour it was wonderful and sad.

2. Tom Hanks

Like Bill Murray, Tom Hanks is just as quick as Letterman and shares a goofy streak. Hanks is hardly ever surly, though, and that combination of attributes might make him the perfect complement to Letterman. They can effortlessly play off each other without the mood ever growing too grumpy. Hanks’ impression of Slappy White yelling “stop bending the shafts!” on Dave’s last NBC episode will probably take up space in my brain that could be better used for anything else until the day I die.

1. Bill Murray

Dave’s first late-night guest will also be his last, with Bill Murray stopping by the second-to-last episode of Late Show tonight. As our TV editor Bonnie Stiernberg writes in an essay that will go up tomorrow, Murray and Letterman shared a Midwestern sensibility, a fundamental niceness that underpins their comedy no matter how sarcastic or absurd they get, and a thinly veiled sadness that deepens the older they get. Their relationship never felt like a perfunctory meeting of host and guest—they were colleagues and friends, two of the most important and influential comedians of the last 35 years, and watching them age together into elder statesmen roles has been bittersweet.

David Letterman’s 11 Best Regular Guests