When Andy Roddick was approached by Ben Stiller to appear in a movie he was producing, about a tennis pro who takes up pickleball, the former world No. 1 turned down the award-winning actor and producer. Repeatedly. “Athlete cameos in movies are normally horrendous,” Roddick says. “I said no to him probably four or five times.”

But this role was no cameo, Stiller explained, and the movie really couldn’t be made without Roddick embodying the protagonist’s childhood tennis rival, who eventually faces off against him in the climactic pickleball match. The guilt trip worked, and Roddick finally agreed to star alongside Jake Johnson in The Dink, which premiered on Apple TV this summer.

The movie is only one piece of the 43-year-old Tennis Hall of Famer’s reemergence into the public eye, after more than a decade when he was seldom seen or heard from. Roddick also appeared in the commentary box and at the analyst desk for ESPN for the first time at Wimbledon in July, and he will return for the U.S. Open this month, all while hosting his twice-weekly show Served, which he has grown into arguably the most popular tennis podcast in the world. Forbes estimates the show generated roughly $4 million in advertising revenue over the past year—much of which goes directly into Roddick’s pocket, along with nearly $1 million in estimated earnings from his combined TV and film work.

“I was always busy in the ten years I was away from the game, so I don’t know that it was a conscious thing,” Roddick tells Forbes of his return to the spotlight. “I think it was more just a snowball effect, and I’ve just enjoyed the stuff I’ve done along the way.”

Considering his crossover into mainstream fame in the 2000s—complete with celebrity relationships, SNL hosting gigs and “Got Milk?” commercials—a second career in tennis media would have seemed like a natural fit after Roddick abruptly announced his retirement in 2013, on his 30th birthday. But at that time,........

© Forbes