In this staff favorite moments segment, producer Josh Weintraub takes us back to his time working on the iconic talk show, Late Night with David Letterman. From his early days as an intern in 1993 to his role as a talent researcher and segment producer on the Late Show with David Letterman from 1996 to 2002, Weintraub shares some unforgettable moments that showcase the wit and humor of the beloved host.
One of the standout moments Weintraub recalls is Dave’s remote segment at an inventor’s convention. During this segment, Dave meets an inventor who created a device to prevent accidental burial alive. To everyone’s surprise, the inventor reveals that he himself had been buried alive not just once but three times. The absurdity of this situation left Weintraub in stitches and solidified his love for the late-night show.
Another memorable occasion Weintraub mentions is when Dave drove through a McDonald’s drive-thru multiple times and pondered whether anyone had ever been killed there or if the shake machine had ever gone haywire and caused harm. Dave’s offbeat sense of humor never failed to entertain.
Weintraub also shares a hilarious anecdote about a guest named Herman McDonald, who was born in a McDonald’s restaurant in 1985. The absurdity of the situation and Dave’s playful banter kept the audience in stitches.
Beyond the comedic moments, Weintraub reminisces about the show’s innovation in showcasing guests’ early work. One guest in particular, Mike Myers, had been a child actor in Canada before rising to fame. Weintraub shares a clip from a sitcom called “The King of Kensington,” which Dave frequently used during Mike Myers‘ subsequent appearances.
The staff at Late Night with David Letterman had unique opportunities to participate in bits and sketches. Weintraub remembers being cast as the lucky fan who gets hit in the head by a pitch from Orlando “El Duque” Hernandez. While the actual hitting was simulated using a dummy, the experience of standing against a brick wall while pitches flew dangerously close made for a nerve-wracking yet exhilarating segment.
As a talent researcher, Weintraub and his team were responsible for gathering information about guests in the pre-internet era. One annual Thanksgiving tradition involved generating a list of pie flavors that Dave’s mom might have baked, as Dave would humorously use his intuitive power to guess the pies’ flavors. The researchers had to scour cookbooks to compile the extensive list, ensuring that Dave’s comedic attempts at guessing kept the audience entertained.
In addition to the behind-the-scenes moments, Weintraub recalls heartwarming interactions with guests. Kathy Lee Gifford‘s farewell appearance on the show led to a surprising retirement gift – a jet ski. Little did the show know that Kathy Lee wanted to keep the jet ski and have it shipped to her vacation home in the Florida Keys, resulting in unexpected expenses.
From surprises gone wrong to memorable impersonations, Weintraub’s time on the show was filled with laughter and unforgettable experiences. Whether it was ruining Jimmy Kimmel‘s planned surprise or getting in trouble with Dave for a viewer mail bit, Weintraub’s journey as a producer was nothing short of entertaining.
Late Night with David Letterman was not just a platform for celebrities. It also brought lesser-known individuals into the spotlight, such as Brother Theodore, an eccentric guest who would sit down with Dave and passionately rant about various topics. The show’s willingness to showcase unconventional and lesser-known talent contributed to its unique appeal.
From the funny and absurd to the heartwarming and nostalgic, Late Night with David Letterman provided endless entertainment. Producer Josh Weintraub‘s favorite moments remind us why this talk show and its host have become legendary in the world of late-night television.
