When Bob Iger was a 23-year-old assistant, he got a $100 tip from Frank Sinatra

Before Bob Iger worked his way up to the CEO of Disney, he started from the bottom, making money scraping gum as a summer janitor and assembling pies at Pizza Hut.

After graduating from Ithaca College in 1973, he took a weatherman job with a tiny cable TV station. At 23, he landed his first gig with ABC.

"I was called a studio supervisor, which was lower than a production assistant," the exec said on "Jimmy Kimmel Live!" "I was the assistant to the production assistant."

While he was low on the totem pole, the gig came with its perks, like meeting legendary singer Frank Sinatra. In 1974, Iger's first year with ABC, the network was televising a Sinatra concert at Madison Square Garden. As the studio supervisor, Iger had to be on hand to run errands for the stage crew.

"I was asked at some point to get Mr. Sinatra Listerine," he recalled, adding: "It's not like there's a Listerine store in Madison Square Garden. So I dutifully ran out and found a drugstore of some sort — this was before CVS — and found Listerine. I came running back, went to his dressing room, knocked on the door and a security person who was about 10 feet tall opened the door. … The next thing I know, Frank Sinatra appears."

Iger handed the singer the mouthwash, and "he handed me a fresh $100 bill."

Iger didn't just bring home a crisp Benjamin Franklin — everyone who worked the concert received a gold cigarette lighter, inscribed Thanks, Sinatra, Iger remembered: "I spent the 100 dollar bill in like five seconds, and I kept the cigarette lighter."

Over the next 31 years, Iger would hold more than 20 different positions at ABC before being named CEO of The Walt Disney Corporation in 2005.

Today, at 68, the Disney chairman and CEO, is worth about $690 million, Forbes estimates. And he still has the lighter. "It's never been used," he told Kimmel, as he pulled it out of his pocket. "It's probably worth about five bucks," he joked.

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