Based on Ebert’s best-selling 2011 memoir of the same name and directed by Steve James — whose nonfiction classic Hoop Dreams Ebert named the best movie of the 1990s — the film is a profound look at the Pulitzer Prize-winning Chicago Sun-Times critic’s life, particularly his treatment for the thyroid cancer to which he would ultimately succumb in 2013, at age 70. Siskel, who was both Ebert’s nemesis as critic for the rival Chicago Tribune and his co-host on their nationally-televised movie review show, died from a brain tumor in 1999, at age 53. And while the two were opposite in just about every way — their opinions of Full Metal Jacket, for hilarious example — one thing they did share, it turns out, was success with the ladies.
Ebert’s libido isn’t exactly a secret. Not only did he champion the work of cult sexploitation director Russ Meyer, he even wrote the screenplay for Meyer’s psychedelic genre mashup Beyond the Valley of the Dolls, which features a car-climax scene even more insane than Cameron Diaz banging that Ferrari in The Counselor. “What did he love about Russ Meyer’s films?” says Ebert’s friend and newspaper colleague John McHugh in the documentary. “Boobs.” McHugh and other old drinking buddies of Ebert from O’Rourke’s in Chicago also offer hilarious reminiscences of his questionable paramours prior to quitting booze and meeting the love of his life, Chaz, whom he married in 1992 when he was 50:
“Roger has always been attracted to weird types. I mean, you should see some of the women that he’s hauled into O’Rourke’s over the years.”
“Back in the old days, Roger had probably the worst taste in women of any man I’ve ever known. They were either gold diggers, opportunists, or psychos.”
“Yeah, I met Roger one time with a woman that looked like a young Linda Ronstadt. And when she was gone from the table briefly, I said, ‘Who is that?’ And he said, ‘She’s a hired lady.’ And I said, ‘A hooker?’ And he said, ‘Now, you take care of her when I leave.’ And he left town. And… anyway.”