Jay Leno

NBC picked him over David Letterman to replace Johnny Carson, and the decision nearly backfired. He debuted as Tonight Show host on May 25, 1992, and trailed Letterman's Late Show for 90 straight weeks before winning the ratings war in July 1995. The turnaround was real: by 2008 he was pulling over 5 million viewers a night, roughly 1.5 times his nearest competitor. He wasn't the obvious choice, but he outlasted everyone who doubted it.

His post-Tonight Show story is misfires stacked on top of misfires. NBC gave him a prime-time hour in 2009; The Jay Leno Show lasted five months and Entertainment Weekly called it television's "Biggest Bomb of All Time." He returned when the Conan O'Brien experiment imploded, then exited for good in February 2014. CNBC gave him Jay Leno's Garage, seven seasons and a Primetime Emmy before cancellation in January 2023. That same month he was recovering from two consecutive accidents: a garage fire in November 2022 burned his face and hands, and two months later a wire across a parking lot clotheslined him off a 1940 Indian Motorcycle, breaking his collarbone and two ribs and cracking both kneecaps. Neither kept him off stage long.

He was doing 300 stand-up dates a year throughout his Tonight Show tenure, keeping the NBC paycheck in the bank. The accumulated result: a net worth estimated around $450 million, a "Big Dog Garage" in Burbank with roughly 341 vehicles in 140,000 square feet, and annual insurance bills around $1.1 million. He has the only privately owned 1963 Chrysler Turbine car. Dyslexic as a kid and a poor student, he had a fifth-grade teacher who wrote on his report card that if he spent as much time studying as trying to be a comedian, he'd be a big star. The teacher was right.