British filmmaker Sebastian Doggart’s film Courting Condi, playing Sunday as part of the Honolulu International Film Festival, is listed as a documentary. That’s half correct, but he’s managed to combine his documentary with a romantic comedy, a drama and, strangest of all, a musical. What happens is a clever, hard-hitting critical documentary that sneaks under the wire with its a goofy premise.

Devin Ratray, (Buzz McCallister from the first two Home Alone movies) plays an alternate version of himself as a failed musician, living with his parents, overweight, poorly dressed and devoid of motivation. But then he finds a purpose, declaring his love for “the most powerful woman in America,” Condoleezza Rice. With the help of Doggart, Ratray decides to learn everything he can about the former secretary of state, but others are skeptical.

“I thought you were gay,” exclaims his mother when he explains his plan.

From there, the two head to Birmingham, Ala., Rice’s home from 1954–1969. It’s here where the film first begins its meld of satire with reality. As Rice’s real-world childhood friends offer insight into her past through stories and photographs, Ratray the actor looks for connections that will confirm their compatibility. When Vanessa Hunter, Rice’s childhood friend, tells Rice’s birthday (Nov. 14), Ratray is ecstatic, exclaiming, “My mother’s birthday is November fourteenth!”

With each new interview, Ratray declares himself more smitten, writing new songs and filming “love discs”—with full-length song and dance numbers—that he’s too scared to send, and so he moves on to learn more.

And we as audience members learn as well. A straight documentary detailing Rice’s rise to power would most likely cover the same basics—that she was raised in the center of the Civil Rights movement, friend of one of the four little girls killed in the infamous Birmingham church bombing, her early interest in classical piano and figure skating, her introduction to politics and her fascination with Joseph Stalin—but it would also be boring. Courting Condi escapes that fate with its absurd interludes, and the fact that most of the interviewees aren’t quite aware of the joke.

That comes through loud and clear when the pair interviews Rick Upchurch, Rice’s one-time fiancé. Ratray sulks in the background, upset to be close to somebody who was so close to his desire. Until, that is, Upchurch admits that the two were never intimate. “She was respectful of her body,” he says, “and that was something she was going to save until marriage.”

“She chose power over love,” Upchurch explains about their breakup. “It’s the first sign of the direction the film will take. From there, Courting Condi veers into the political morass that has been Rice’s life, from controversies of her time at Stanford University through 9/11 and the Iraq War. As ugly truths are revealed, Ratray has to reexamine his infatuation, and we as an audience are as repulsed as he is.

Courting Condi plays Sun 3/8, 12:35PM, Hilton Hawaiian Village Beach Resort, 2005 Kalia Rd., www.honolulufilmfestival.com.

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