For many baseball lifers, retirement from playing leads seamlessly to a gig as a bench coach or a TV talking head. For Todd Zeile, it led to a trip to Scotland with Charlie Sheen to find the Loch Ness monster. “One night we went out on this tiny wooden rowboat, with a bottle of Scotch,” he recalls. “I did the rowing. It was cold and dark. Calm—but kind of ominous.” So: Any sightings of Ol’ Nessie? “Well, Charlie will tell you we almost got capsized because of a very mysterious undercurrent.”
It’s a radiant May afternoon in the San Fernando Valley, and Zeile is having lunch on a terrace at a country club near his home, explaining how a mild-mannered major-leaguer became bros with a notorious Hollywood bad boy. When he retired from baseball in 2004, Zeile sought an alternative to the traditional ballplayer afterlife. He dabbled in real estate (getting burned when the market tanked in 2008). He tried his hand as an aviation entrepreneur (with better luck).
And then there’s the Hollywood thing: Over the past decade Zeile has worked as a film and TV producer, enjoying his biggest success with Sheen’s sitcom Anger Management. But he has also hit plenty of bumps along the way, learning that if there’s one thing as hard as making it in the major leagues, it’s making it in entertainment.
His former manager, Joe Torre, calls Zeile the Forrest Gump of baseball, and the movie analogy holds true: He’s played a supporting role in some historic moments. Over 16 seasons, Zeile played for 11 teams. He played third base for the Baltimore Orioles alongside Cal Ripken the night the Hall of Famer broke Lou Gehrig’s consecutive-games streak. He played in the first Subway Series between the Mets and the Yankees, and was the Mets’ first baseman the night baseball returned to New York City after 9/11. And Zeile wasn’t merely a wallflower: He was one of the top power-hitting third basemen of the 1990s, retiring with 253 homers and 2,004 career hits.
Zeile made his first foray into business in his playing days. In 2002, after a midseason trade, he wondered how he would get his family to fly to visit him, and had the idea of starting a company to charter flights for athletes and celebrities. Zeile partnered with Bill Borgsmiller, the president of a small aviation firm. With Zeile as an investor and rainmaker, Aviation Consultants Inc. grew its fleet from two planes to 10 and is thriving today. “Nothing rattles Todd … and as you go through ups and downs, that’s a very good thing,” says Borgsmiller.
Having grown up in Los Angeles and played in New York and L.A., Zeile had long been intrigued by the entertainment industry. During his playing days, he invested in the movie Dirty Deeds, a high school comedy. Zeile even had a bit part, as a mullet-wearing street bum. “I thought, Hey, this is fun,” he says. “This gives me something to transition into.” But Dirty Deeds, released in 2005, was critically panned, and Zeile lost millions, “more than I would have paid in tuition if I’d gone to film school for 10 years,” he says. “It was a great education, but a costly one.”
One frigid night in 1998, when Zeile played for Los Angeles, he was in the Dodger Stadium tunnel warming up his hands before an at bat when he heard a voice boom, “Dude, can you point me to my seat?” It was Sheen, who had just wandered in from the parking lot. A baseball fan whose screen roles included star turns as an erratic pitcher in the Major League movies, Sheen recognized Zeile too.
The two eventually became friends and travel companions. Over the years they’ve played catch—over glaciers in Alaska, while swimming with dolphins in Cabo, and at countless ballparks. “People don’t get it,” Zeile says of their relationship. “I’ve never been a partier. I don’t drink. For whatever reason, I became a solid influence for Charlie.”
That opened the door to Zeile’s biggest role yet in Hollywood. In 2011, Zeile was looking for a new project after financing I Am, a retelling of the Ten Commandments story. Sheen was doing a comedy tour, and Zeile was on the bus with him coming up with bits, when the news came that Sheen (whose contract demands and behavior had been making headlines) had been dismissed from his TV series, Two and a Half Men.
Pondering his next move, Sheen got excited about a pitch of Zeile’s—a show in which a former baseball player copes with life after the game. The two retooled the idea, and it became part of the DNA for Anger Management, in which Sheen starred as a baseball player-turned-therapist. Zeile was a co-executive producer, an amorphous title: In practice, he was on set every day to keep Sheen focused and chime in on story ideas. The show’s pilot, which aired in June 2012, attracted 5.74 million viewers, making it the most watched sitcom premiere in cable history, and the series had a breathless 100-episode run that ended in December.
Anger Management gave Zeile a steady paycheck and a track record that may help him line up future work; he and Sheen have been discussing new film and (non-sitcom) TV projects. Zeile is also working with an investment group, G2, on an initiative to bring water-purification products to developing countries. He’ll be spending a week in Ghana and other African nations this summer, meeting with local officials. But his primary focus is hustling in Hollywood, with the plug-away mentality that served him well in baseball. “I can say that all this has led to some interesting adventures,” he muses.
A version of this article appears in the July 1, 2015 issue of Fortune magazine with the headline “A Former Slugger Seeks Hits in Hollywood.”