One of my favourite trivia challenges is “Name the three Oscar-winning actors who have appeared in Madonna videos.” The other day, someone tripped me up by pointing out that, technically, Warren Beatty counts. However, his one and only competitive Academy Award is for directing Reds. He’s been in other Oscar-winning films—including the one for whose soundtrack that Madonna video was made—and in fact every movie but one for which he was himself nominated won at least one Oscar. (New trivia challenge: name the outlier!) However, he’s actually made surprisingly few movies for a man whose first movie was in 1961 and who retired from acting in 2016—though he swears he’s making a Dick Tracy sequel at some point.

As a child, Warren Beaty (the family name only has one “t”) allegedly did a killer Milton Berle impersonation, something I would love to hear. His big sister Shirley, who took their mother’s maiden name of MacLaine, says he would sing along to Al Jolson records. What with one thing and another, it seemed likely he would go into acting. It didn’t help that he had the kind of clean-cut, all-American good looks that made him perfect for the wealthy Milton Armitage on The Many Loves of Dobie Gillis—making him one of the few Oscar winners to have appeared on TV with Bob Denver, I suspect.

Everyone seems agreed that Beatty quit the show, but I haven’t learned why. It seems likely to me that he wasn’t interested in a continuing sitcom role; it doesn’t seem his style. It’s hard to picture now how different Hollywood would have looked if he’d kept the job. Still, in 1961, he was in Splendor in the Grass, with Natalie Wood. A few years later, he was Clyde Barrow. From that point, he was an icon in Hollywood. He’d produced the movie, helping to get it made over Jack Warner’s objections that gangster pictures went out with Cagney.

All told, he has acted in a mere twenty-five movies, and that’s if you consider a music video that ties into Bulworth to be a movie. (It’s four minutes long, but IMDb doesn’t list it as a short. Your guess is as good as mine.) I’ve long joked, in fact, that the theme of Beatty’s career is “don’t give Warren Beatty money.” It can be about the behind-the-scenes drama of a movie or the movie’s actual plot, as in McCabe & Mrs. Miller, but either way, it does seem to come up surprisingly often for such a sparse career. It’s not universal, but it happens more than you might expect.

He has had a few strange successes, including the passion project Reds, but I wonder if what he’ll be best known for will be holding onto the Dick Tracy rights. Now, I like Dick Tracy, thought I will die on the hill that the wrong song from it won Best Original Song. Still, Beatty’s been holding onto the rights for decades now, insisting that he’ll get around to making another movie of it Just Any Day Now. Someone could be doing something with it. I’ll admit that there’s no reason to assume that what they’d be doing was good; it was improbable that his version would be as good as it was. But still.

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