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