Adapting a book of short stories by postmodern master David Foster Wallace is an ambitious task for any screenwriter, but it's an especially impressive undertaking for a first-time filmmaker. The Office actor John Krasinski makes his directorial debut with this bleak comedy that boasts a talent-filled roster of actors, but its loosely connected source material probably should have stayed on the shelf, rather than venturing onto the screen. Julianne Nicholson stars as Sara, a graduate student whose recent, painful breakup drives her to begin studying men. Each person she interviews reveals a startling mean streak, especially when it comes to women. Subject #3 (Christopher Meloni) recounts a story where he seduces a woman whose beauty is matched only by her vulnerability. Subject #11 (a hilariously slimy Will Arnett) tries hitting on Sara, even as he is pleading with his girlfriend to let him into her apartment. Subject #2 (Josh Charles) uses the same lie-filled script to exit a number of relationships. Subject #15 (Michael Cerveris) is ashamed of his angry outbursts and the inevitable violence that follows. Krasinski earns credit for choosing to play perhaps the film's worst man, Subject #20. On The Office, the actor plays archetypal nice guy Jim Halpert with a smiling, smirking ease, but here that charm is intentionally gone. It's not an enjoyable performance to watch, but it demonstrates that Krasinski has more range than some might have expected. The rest of his cast -- including Timothy Hutton, Ben Shenkman, Chris Messina, Lou Taylor Pucci, Max Minghella, Bobby Cannavale, Dominic Cooper, and Death Cab for Cutie frontman Ben Gibbard -- display equal talent in their work, sparking both laughter and shudders while their characters misbehave. For all its dark humor, this is not a pleasant film, though it likely wasn't intended to be. If taken as a statement on human (or masculine) nature, it's a damning indictment of the species. The main problem of Brief Interviews with Hideous Men is its lack of focus, though it's tough to tell whether that originates in the source novel or in Krasinski's adaptation. Almost all the stories focus on men's indignities toward women, but a single tale starring veteran character actor Frankie Faison veers off the script's prescribed road. As Subject #42, Faison explains his embarrassment regarding his father's lifelong job as a bathroom attendant. It's a beautifully shot, finely acted scene, but it doesn't fit with the rest of the film in theme or tone. Though most scenes last only seconds or a few minutes, this account seems to take up a hefty part of the film's 80-minute run time. For all its faults, Brief Interviews with Hideous Men isn't a failure. The cast is enormous -- and enormously talented -- with everyone giving strong performances in their brief appearances. Krasinski's idea to add the frame story of a graduate student doing interviews helps bring the film together, though it never fully coheres. Each scene stands individually, but the movie doesn't work as a whole. However, Krasinski makes interesting choices as a director and screenwriter, and he reveals a promising style that could be better matched with a less overreaching film.