TIME Television

See David Letterman’s Top 10 Sidekicks and Guest Stars

From Richard Simmons to Dave's mom

Here are ten of the guest stars and side kicks who helped David Letterman create such spectacular television.

  • Paul Shaffer

    The colorful Canadian bandleader was really two sidekicks in one: an Ed McMahon—Doc Severinsen hybrid with the talent to back up A-list guest musicians and the ability to banter with Dave as an equal. Perhaps more essentially, Shaffer served as the simple syrup to Letterman’s bitters, undercutting the host’s grumpiness with wacky irreverence.

  • Larry “Bud” Melman (Calvert DeForest)

    A celebration of oddness, actor Calvert DeForest was an awkward, unassuming Truman Capote lookalike and soundalike who came off like a stranger trying to befriend you on a bus—the guy you’d prefer to avoid but can’t help liking. As Melman, he was Dave’s clutch hitter, used for everything from serving as New York’s official greeter at the Port Authority to appearing in commercial parodies for Toast on a Stick. Whatever strange errand he ran, his warm humanity was always apparent.

  • Dave’s Mom

    When a man is as uncomfortable in his own skin as Letterman, few things are more squirm-inducingly funny than watching him deal with his mother. Dave’s mom Dorothy Mengering was a frequent guest, baking pies on the show every Thanksgiving and serving as a correspondent for three Olympics. Viewers lapped up her small-town charm, and she explained her appeal like this: “People enjoy seeing a mother and son together.”

  • Chris Elliott

    Late Night writer Chris Elliott was the incarnation of the show’s sense of the absurd. His characters, like the Guy Under the Seats, were often just thin disguises of his own frustrated and bitter showbiz-failure persona, made brilliant by the crumbling of Elliott’s cheery facade.

  • Rupert from the Hello Deli

    Letterman smartly deputized Times Square denizens as co-stars, and Rupert Jee, owner of the Hello Deli, was up for any game or prank, including approaching strangers with a hidden earpiece and repeating whatever Letterman said. His unassuming manner lent great comedic contrast to Dave’s bizarre instructions, leading to such moments as Rupert posing as a newsstand vendor and offering to remove his pants with every purchase.

  • Richard Simmons

    Simmons was the show’s Tasmanian devil, a cheerleading dervish delivered to earth in inappropriate short shorts to make Dave cringe. Dave’s insults and Simmons’ defensive yet loving incredulity gave the pairing an opposites-attract spark.

  • Mujibar and Sirijul

    The Bangladeshi souvenir salesmen became Letterman’s roving correspondents. Stiff yet friendly in ill-fitting suits, they gave halting responses to his queries that helped serve Dave’s deconstruction of the conventional wisdom about what constitutes entertainment.

  • Tony Randall

    One of the Late Show’s most frequent guests, with 70 appearances, Randall would stop by for a chat or surprise the audience by popping off a quick joke from the cheap seats. Randall’s acquiescent warmth created a wonderful, watchable bond with the host.

  • Alan Kalter (announcer)

    A kinetic presence with psychotic tendencies, Late Show announcer Kalter became a powerful character. Kalter’s fictional (we hope) dark side kept a hostage in a metal locker and cursed Dave for ignoring him. As Letterman grew warmer and more personable, Kalter’s character insured that the show’s bitter aspects remained part of the mix.

  • Harvey Pekar

    Letterman and comic-book memoirist Pekar had an uneasy bond. They didn’t seem to like each other much, turning insult-filled interviews into compelling can’t-turn-away TV. Letterman once banned him from the show, but given their chemistry, it’s unsurprising that the ban didn’t last.

TIME Television

See David Letterman’s Top 10 Best Late Night and Late Show Moments Ever

From the Alka-Seltzer suit to his post-9/11 monologue

Among the reasons David Letterman became the king of late night is his ability to create or conjure memorable moments. Here are ten of the best.

  • Bill Murray is Dave’s first guest (1982)

    For Letterman, Murray has dressed like Liberace, a Kentucky Derby jockey and a Renaissance fop. His first visit set the tone of the show when, after a long rant in which Murray decried the host’s “mind games,” Letterman responded, “Now that you’re well-known, is it harder to be funny?”

  • Andy Kaufman challenges wrestler Jerry Lawler to a match (1982)

    In a hoax bit, comedian Kaufman got pro wrestler Lawler to slap him in the face as Letterman smirked behind the desk. The stunt confirmed Dave’s status as a comedy chaos magnet—a master at remaining calm while hysteria swirled around him.

  • Dave gets dunked in a suit made of 3,400 Alka-Seltzers (1984)

    What some do for science, Dave did for comedy. With a snorkel and goggles in place, Dave was dunked into a fizzy experiment in laughter. He’s helpless in his harness, floating in an effervescent water tank surrounded by the volcanic chaos of bubbles. The experiment was duplicated with the likes of sponges, marshmallows and velcro, showing how far Dave would go for a laugh.

  • The very first top 10 list (1985)

    “Heats.” “Rice.” “Moss.” These were the initial entries in the show’s first Top 10 list, “Things That Almost Rhyme With Peas.” Sometimes presented by politicians, celebrities, sports champions and everyday heroes, the lists—more than 4,600 of them—became Letterman’s signature bit.

  • Cher calls Dave an a–hole (1986)

    Dave’s meta-deconstruction of the late night form led to uncomfortable truths — such as in this segment, where an interview with Cher centered on why it took four years for her to agree to appear on the show. Her casual reasoning — “because I thought you were an a–hole” — became part of the show’s disarming folklore.

  • Madonna won’t stop stop cursing (March 31, 1994)

    Letterman often had a flirty effect on female guests, causing many to leave filters at the door. Here, Madonna and Dave giggled and teased, discussing their underwear and making innuendos. Madonna sweetly told Dave he was a “sick f-ck.” Never has that term sounded quite so loving.

  • Drew Barrymore flashes Dave for his birthday (April 12, 1995)

    The Late Show with David Letterman
    Alan Singer—CBS/Getty Images

    In a ’90s version of Marilyn Monroe’s “Happy Birthday, Mr. President,” a 20-year-old, braless Barrymore surprised Dave with a dirty dance on his desk, followed by lifting her shirt. Dave’s reaction—confused but joyful surprise—contributed to the buzz.

  • Dave gets personal (2000 & 2009)

    It’s one thing to be a great host with a knack for comedic moments. It’s another entirely to tap into the national psyche. Dave was long regarded as the king of irony, but that died in 2000, when he dropped all comedic facades to pay tribute to the surgical team that saved his life. It was a rare but powerful moment when Dave the host became Dave the man—a feeling that would be replicated as his messy personal cheating scandal went public nine years later—and his brittle realness drew us even closer to the legend we thought we knew.

  • Dave gives a heartfelt post-9/11 monologue (2001)

    The first late-night host to return to TV, Letterman gave viewers real catharsis following a national tragedy. His eight-minute introduction was halting, honest and vulnerable, tapping into our collective fear and sadness. By the end, he also provided what we needed most: courage and hope.

  • Joaquin Phoenix is bizarre and rambling (Feb 2009)

    Phoenix devised a meta-hoax that found him growing a long beard and claiming to have left acting for hip-hop. Included in this, for reasons not quite clear, was appearing on Letterman like he had no idea what was happening around him. Letterman fired questions at Phoenix despite the guest’s inability to string together a sentence. Ending the interview with, “Joaquin, I’m sorry you couldn’t be here tonight,” cemented the segment as a classic.

TIME remembrance

Robin Williams: Comic Jen Kirkman Says He ‘Wasn’t Jaded’

Robin Williams Death
Paul Drinkwater—NBC/Getty Images; Reed Saxon—AP

"He just really wanted to see what young people were doing and laughing at," she says

Robin Williams, who died Monday at age 63, won an Academy Award in 1998 for his role in Good Will Hunting. But Jen Kirkman, a stand-up comic, author and longtime Chelsea Lately panelist, saw firsthand how winning acting’s highest dramatic honor did nothing to curb Williams’ humility or his love for comedy. She remembers the late actor as supportive of young talent:

“He was coming to UCB in LA a lot to watch any kind of comedy show he could — stand-up, improv, whatever. Robin was the first truly famous person I’d ever encountered who walked backstage, assumed everybody was a comic, treated them as such, and acted like, ‘Is it OK that I’m here? Don’t make a big deal, I’m not trying to get in the way.’ He would watch the show, then come backstage and compliment you specifically on stuff he saw. I remember chatting with him about [how] he was about to go on this big Australian tour, and he was just excited and nervous. He just really wanted to see what young people were doing and laughing at.

He was so warm and nice, and a genuine feeling of, he’s not taking himself too seriously. He won an Oscar for dramatic acting, and you would never know it. He was humble and graceful and polite. He was just nothing but excited to be around this new energy. He wasn’t jaded, or, ‘Lemme tell you kids how it used to be.’ I really liked being in his presence. I found it very fascinating — like, that’s how you wanna be.”

TIME remembrance

Bill Maher: ‘You Could Just Tell There Was a Humanity in Robin Williams’

Robin Williams Death
Mireya Acierto—Getty Images; Jeffrey Mayer—WireImage/Getty Images

Williams "only let you see so much," Maher says

Robin Williams, who died Monday at 63, knew the secret to being a good television-show guest: adapting to the program without losing yourself. Not everyone can do that, says Real Time host Bill Maher, but Williams could do it as well as, if not better than, anybody on his show.

Here, Maher remembers Williams’ shape-shifting comedy:

“Robin and I had a nice friendly relationship. I can’t claim I knew him well, but honestly, I don’t know how many people did. He seemed like the kind of guy who didn’t open up to a lot of people. That is not unusual in this business. I know a number of people I would count the same way, and some of these people I know a lot better than Robin, comics I’ve known for 35 years and spent tons of hours with, and I still don’t really know them, because they only let you see so much, and they speak through their art.

The thing about Robin that I loved the most — and again, with limited experience — is that when he did my show, he was so great at it, because he was able to achieve something that eludes a lot of comedians who have tried to do Real Time. It’s not an easy show to do, because you have to be very smart about politics. We don’t use a lot of show business people on the panel. I can name the show business people who can do it on a couple of hands — Ben Affleck, George Clooney, Alec Baldwin, Kerry Washington — people who are very politically aware and involved, and that is their passion. But mostly, show people don’t do it — we have them on, but in one-on-one settings in the mid-show. But Robin did the panel, and he was able to both modulate his normal manic persona down to what was appropriate for the show he was doing, and also, completely still be Robin Williams. That is not an easy trajectory to find, and he did, and I always loved him for it. First of all, it means you’re humble — that you understand that you have to shape-shift a little to the show you’re doing. Some people don’t do that. Some people just refuse to do that. They wanna be exactly who they are, on whatever show they’re doing. I don’t agree with that. I think when you’re the guest, you have to bend a little. He did that. He was still Robin Williams, but he was exactly right for the show he was doing.

His style, when it came on the scene, looked completely new to people, and in many ways it was. He was fast and furious, and I think there’s something else that’s behind there that you can’t really quantify or define, but you could just tell there was a humanity in Robin Williams. He seems like a genuinely nice guy, like a good person who cares and tries to give back to the community. Some people, you get the impression that they’re putting on an act all the time. I didn’t get that impression with Robin Williams. I didn’t know him well, but I always thought, there’s a very decent person there.”

TIME remembrance

Joan Rivers: Why Robin Williams Was a Great Red Carpet Interview

Robin Williams Death
Bruce Glikas—FilmMagic/Getty Images

"You popped the champagne cork when you said hello to him," she says

Joan Rivers, who died on September 4 at the age of 81 after complications from throat surgery, reflected on Robin Williams the month before her death.

Joan Rivers is an authority on red carpet interviews — and the veteran comedian says Williams was one of the best celebrities to chat with, both for his candor and his zany humor. Below, Rivers reflects on his more serious roles:

“Robin was one of the great interviews. You’d see him coming down that red carpet and you knew, OK, now we’re gonna have fun. We’re not gonna hear the usual, ‘Yes, we all love each other on the set.’ The one I remember most is, I had this incredible dress, I think it was Dior, with great big gold feathers on the top, absolutely beautiful. I was looking so snappy, I thought. And he came up and did five minutes on looking for eggs in my top, because I looked like a chicken. It was fabulously insane. He made like a chicken, and was clucking, and looking for eggs. Hilarious.

He was very wild. The only one you could compare him with in terms of style was Jonathan Winters. Both of them crazy mad, going into characterizations, in and out, in and out. Such ADD. It’s like you open the capsule and everything came out, all the air came rushing out. You popped the champagne cork when you said hello to him.

He was an incredible actor. [His comedy bits] were all acting bits. They may have been funny, but he became the crazy man, he became the duck. You forget, for all the things he did, he also did Waiting for Godot on Broadway, he did Bengal Tiger at the Baghdad Zoo. I was waiting for him to do King Lear. I think he would have been great. He came from Juilliard with Patty Lupone and Christopher Reeve. That was a big class he came from. He also had a really formal upbringing. He came from an upper middle class family, very educated, very well-read, very knowledgable about everything, about literature. The references would be so amazing. Even to do Dead Poets Society, he knew what he was talking about when he was talking about the poetry. He was incredible. Everyone’s talking about the comedy, but I’m talking about The Fisher King, What Dreams May Come, Awakenings. Everyone forgets all the serious, wonderful things he did, not just Mrs. Doubtfire.

We all flew into New York to do a Richard Pryor roast, and everybody was on the dais — Don Rickles, David Brenner, Garry Shandling, All of comedy was on the dais at the Waldorf Astoria. Next to last was Robin, and he blew everybody out of the ballpark. He was so above all of us. He was incredible. Very special.”

TIME remembrance

Gilbert Gottfried on Robin Williams: “It Was Such a Workout Playing Off Someone Like That”

Robin Williams Death
Dave Kotinsky—Getty Images; Vera Anderson—WireImage/Getty Images

Williams was "the same onstage and off," Gottfried says

It wasn’t easy keeping up with Robin Williams, who died Monday at age 63. Comedian and friend Gilbert Gottfried described joking around with the late actor as dizzying. Here, Gottfried remembers the first time he met Williams:

“We would run into each other at comedy clubs when he’d be on stage, and we’d riff off each other. That was always very invigorating, because with someone like him you had to keep on your toes every second. I don’t really remember much about the times we were on stage because it was so strenuous. It was such a workout playing off someone like that, that when I got offstage, I was pretty much dizzy afterwards.

He worshipped Jonathan Winters, and you definitely could see the similarities. One big one is that they were the same onstage and off. Every now and then he would talk seriously, but more often than not, he was that guy. Every now and then, another part of him would pop up that was quiet.

The first time I met him, he showed up at the Improv. I was supposed to go on next, and they told him he would go on next, and he said, ‘Let Gilbert go on, because there are some people in the audience and I want them to see him.’ Then, when I got off stage, I was very pleased that he was laughing and rubbing his eyes. He went, ‘Oh, you really baked my cookies.’ I wasn’t quite sure whether to take it as a compliment.”

TIME remembrance

Lewis Black Remembers Robin Williams: He Was “On Another Level”

Robin Williams Death
Kevin Winter—Getty Images Lewis Black and Robin Williams

Williams was as smart as he was funny, the comic says

Contrary to popular belief, Robin Williams, who died Monday at the age of 63, wasn’t “always on” and going a mile a minute. But comedian Lewis Black says Williams’ ability to jump from one topic to another was unparalleled among his peers. Here, Black remembers Williams as an endlessly giving and energetic person:

“I had met him before, but I really got to know him when we went on two USO [United Service Organization] tours together [in the late 2000s], and spent time with him on the film Man of the Year.

The first thing was: I got on a plane with him, and he was reading a book which was a history of Iraq. He sat there and talked about it for 35 minutes, going through the history of Iraq with us. That’s astonishing. I thought, this guy is kind of brilliant. He was a really bright guy who may have had a photographic memory.

[Trying to figure out how he does what he does] is like standing in front of a hurricane and going, gee, I wonder how that happened.

He wasn’t someone who was always on. It’s very much a misconception.

There were jokes of his that made me laugh hard, but it was the going from one thing to another, making those connections. It’s like how you watch an improv group take suggestions. It was like Robin had the most brilliant audience inside his head throwing out suggestions, because he would put combinations together that were just crazy. And how he could work out of the moment. That working out of the moment is a gift, but he did it on another level.

[On the USO tours], the amount of energy he brought when we would get off of a helicopter and walk towards the troops — the amount of energy he gave to them was unbelievable. It was really incredible to be in that kind of giving presence. I was exhausted. We’re going from place to place, he can’t give enough to them, and I’m trying to think, ‘Where can I take a nap?’ It was inspiring. Wherever we’d land, until the point where we would leave, he’d be talking to them — and not just going off, but being straight with them. I adored him. If you look at the outpouring that’s gone on, that someone of his stature would come to see them was kind of amazing to them.

It’s proof again that the good die young, and pricks live forever. He’s gonna be missed. There’s a hole, and it’s gonna take a long time to be filled.”

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