Jay Leno (Part 3)

·29 min·2 clips

Jay Leno tells the story of how he accidentally booked the wrong Kathie Lee as a guest on the Tonight Show.

Jason Fraley opens with an entertainment-history setup. He gets from the Hollywood Casino at Charlestown Races booking to Jay Leno talking about the Tonight Show, Johnny Carson, David Letterman, and Arsenio Hall without much fuss. Then Sean Connery takes over. Leno remembers him less as a smooth Bond icon than as a loud, tough Scotsman with a fighter's edge and a taste for dirty jokes. Fraley keeps tying the story back to the movies people know: James Bond, Indiana Jones's dad, and the funny age gap baked into that casting. Leno's impression carries a lot of the fun. Connery turns into this Savile Row-suited force who laughs like a pirate, asks for the newest joke, and somehow makes a tiny Tonight Show dressing-room shower feel like a stage. The details sell it. Leno says Connery used the shower, sang "Scotland," and scared the newsman badly enough that people downstairs wondered who was screaming. Fraley catches the references as they fly by. He drops "Don't call me junior," then nudges the conversation back toward Leno's favorite guests and the wider Tonight Show world. Nothing gets too polished. Leno's affection shows up in the odd stuff: the cheap car story, the secondhand Jensen, and the gap between movie-star money and stubborn Scottish practicality. He is not giving Connery a museum label. He is piecing him together through jokes, habits, voices, and backstage weirdness. The ending returns to awards talk, Twain winners, and a brief Kennedy Center question before Fraley lands back on the casino date. The pitch is plain enough: Jay Leno and Arsenio Hall on one bill, with Fraley clearly glad to have Leno back.

As heard by us

Jay Leno turns comedy history into sharply remembered Sean Connery stories and Tonight Show touchstones.

Jay Leno's talk with Jason Fraley takes a relaxed, long-view pass through a comedy career defined by the people, routines, and rivalries that still stick.

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Why you'd press play

You want Jay Leno on Johnny Carson, late-night rivalries, and Tonight Show stories that still have mileage.

Read the full recommendation in PlayNext →

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