--- title: David Letterman: Top 10 Sidekicks and Guest Stars description: From Richard Simmons to Paul Shaffer, these are David Letterman's top sidekicks and guest stars. canonical: https://time.com/3849750/david-letterman-sidekick-guest-star/ author: Larry Getlen article:opinion: false article:content_tier: free article:published_time: 2015-05-19T13:30:01.000Z article:modified_time: 2026-02-22T06:59:49.015Z article:section: Entertainment og:title: David Letterman's Top 10 Sidekicks and Guest Stars og:description: From Richard Simmons to Dave's mom og:url: https://time.com/3849750/david-letterman-sidekick-guest-star/ og:site_name: TIME og:image: https://static.time.com/v3/assets/bltea6093859af6183b/bltde093bcdab65f2d0/6988d9b9bc6cfc69913e2a3c/time-logo.jpg?branch=production og:image:width: 1200 og:image:height: 675 og:image:alt: TIME og:type: article twitter:card: summary_large_image twitter:title: David Letterman's Top 10 Sidekicks and Guest Stars twitter:description: From Richard Simmons to Dave's mom twitter:image: https://static.time.com/v3/assets/bltea6093859af6183b/bltde093bcdab65f2d0/6988d9b9bc6cfc69913e2a3c/time-logo.jpg?branch=production --- # See David Letterman's Top 10 Sidekicks and Guest Stars > Sponsored content. 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Terms and conditions apply. * Savings buckets are a feature of Ally Bank's Savings Account. * No ATM fees from Ally Bank at Allpoint and Moneypass ATMs plus we reimburse for fees charged by other ATM owners nationwide up to $10 per statement cycle. * Early direct deposit offers eligible direct deposits up to two days sooner. * Spending buckets are a feature of Ally Bank's Spending Account. by [Larry Getlen](https://time.com/author/larry-getlen/) ## Larry Getlen May 19, 2015 1:30 PM UTC by [Larry Getlen](https://time.com/author/larry-getlen/) ## Larry Getlen May 19, 2015 1:30 PM UTC 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. 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