When Stern had Jake Gyllenhaal on the show, he pressed the actor to talk about doing a love scene with Jennifer Aniston. Stern knew that Gyllenhaal had a longtime crush on the “Friends” star.
Gyllenhaal shared what happened when filming with Aniston making “The Good Girl” (2002). He said it was torture. He revealed that she used the “pillow technique.” She told him she was going to put a pillow between them. Problem solved.
Robin and Howard roasted the actor who played “Star Trek’s” Captain Kirk for a full five minutes before he even entered the studio. Stern demanded to know why everyone he works with hates him. He played a clip of George Takei dissing his former castmate at a previous Stern show.
But Shatner brushed it off, claiming nothing the “Sulu” actor said is true. Stern worked hard to dig up old unflattering stories. He pressed Shatner about how much he lost in his first divorce settlement and that the proud man lived in his truck after “Star Trek” went off the air in 1969.
Howard Stern has a way of getting celebrities to share extremely private stories. When he hosted Stephen Colbert, just as the Comedy Central host was taking over the desk at “Late Night with David Letterman,” he opened up about a painful family tragedy.
His father, a dean of medicine at Yale, and two of Colbert’s older brothers died in a terrible plane crash. Colbert, the youngest of 11 children, was left traumatized from losing a father he loved deeply and his brothers. He thinks perhaps the role of keeping his mom smiling with his humor shaped his dreams of becoming a comedian.
Howard Stern and Bill Maher locked horns and engaged in a bitter feud more than 20 years ago. It was during the buildup for the War on Terror after the Trade Center events. Maher, provocative as always, said something incredibly offensive to the US military and Stern was not having it.
He banned the outrageous HBO political host. Finally, in 2019, Stern invited Maher back to the radio show and they buried the hatchet.
Paul Rudd stopped by the Howard Stern Show in 2015 and he dished a doozey. Rudd told the story about how he got dubbed “Donny the Dweeb.” It happened after he got a part-time job as a DJ. He was about 18 and did weddings and bar mitzvahs.
At one gig, he was in a funk and began dancing like a spaz. His boss grabbed the mic and introduced him as, “Donnie Dweeb.” It stuck. His silly jig became known as “the dork dance.” Kids would ask him to do it. He also talked about speaking with Stan Lee about the intricacies of the Antman. (Who’s a dork now?)