Gary's Outfit Gets Roasted, Then He Considers Braces | Howard Stern Show 2026

Gary Dell’Abate catches heat for what he wore during Howard Stern’s Letterman appearance. The conversation moves from Gary’s clothes to his teeth when he reveals that he has an orthodontist appointment and is considering braces. Howard, Robin, Ralph and the crew have plenty to say about both. The episode also includes Jeff the Drunk’s call, Howard’s account of a long-standing misunderstanding involving David Letterman, and Gary’s visit to a chocolate shop for Howard TV. CHAPTERS 00:00 Richard Christy’s movies and Robin 00:50 Jeff the Drunk calls Howard 03:09 Howard revisits his Letterman appearance 06:26 The Letterman party misunderstanding 12:09 Gary’s outfit sparks a studio roast 15:50 The Russian dressing story 19:45 Callers question Howard’s Letterman appearance 21:35 Howard discusses his relationship with Letterman 24:57 Letterman’s comments about therapy 25:35 Gary and the Chocolate Factory 26:51 Gary reveals his orthodontist appointment 29:49 Gary explains why he wants braces 32:15 Yucko calls in KEYWORDS Howard Stern, Howard Stern Show, Stern Show, Classic Howard Stern, Stern Show Highlights, Stern Show Clips, Radio Comedy, Gary Dell’Abate, Baba Booey, Gary braces, Gary teeth, Gary Letterman outfit, David Letterman, Jeff the Drunk, Yucko the Clown #howardstern #howardsternshow #sternshow #ClassicHowardStern #SternShowHighlights #SternShowClips #radiocomedy