A Romantic Comedy About Two Straight Men: John Hamburg’s I Love You, Man Might be the First Dude Flick With a Heart

After graduation and a year of living at home, Mr. Hamburg attended N.Y.U. Film School. In his first year, he made a short called Tick, featuring Mr. Showalter, which made it into the 1996 Sundance Film Festival. Mr. Hamburg arrived in Park City with the script for his first feature, Safe Men, in his suitcase. Starring Sam Rockwell, Steve Zahn, Mark Ruffalo and Ms. Kirk, Safe Men has grown into a cult favorite—particularly among comedy writers—but in 1998 it wasn’t exactly gangbusters in theaters. “It made 52,000 dollars,” Mr. Hamburg said. “I was pretty depressed.” But one person who did see it and was impressed was Ben Stiller, who brought Mr. Hamburg on to work on Zoolander, and eventually Meet the Parents, which Mr. Hamburg credits as his big break. Mr. Stiller would also star with Jennifer Aniston in Mr. Hamburg’s next directorial effort, Along Came Polly, in 2004.

Mr. Hamburg directed a few episodes of Undeclared, the still-underappreciated Judd Apatow show that starred Seth Rogen and Jason Segel and other names now familiar to anyone who wonders how this small group of dudes keep showing up in each other’s movies. In fact, they appear with each other so often, one could be forgiven for getting the impression that Mr. Rogen, Jonah Hill, Mr. Segel, Mr. Rudd, Jay Baruchel and all the other guys of Knocked Up, Superbad, Anchorman and Pineapple Express are hanging out in each other’s basements, playing video games and cracking jokes while occasionally taking breaks to make movies that gross over $100 million. But, as much fun as they all clearly have working together, it is still work and Mr. Rudd and Mr. Segel both made sure to praise Mr. Hamburg’s tightly structured script and work ethic. (After days of doing press for the film, Mr. Segel said he’s just mainly asked why he looks so fat in the now infamous Vanity Fair Annie Leibowitz photograph featuring he, Mr. Rogen and Mr. Hill in flesh-colored body suits with a fully clothed Paul Rudd. “Paul got lucky in that suit,” Mr. Hamburg said. “The sad thing is, all four of those guys go to the same personal trainer. And that is not a joke.”)

I Love You, Man started out as a pitch by writer Larry Levin called Let’s Make Friends. It was brought to the attention of Mr. Hamburg, who continued to think about it over the years. “I just loved the premise and thought there was a movie about male friendship that was there to tell,” Mr. Hamburg said. He started to make notes and couldn’t stop. “I’m writing about a world I can relate to.”

Case in point: When told that Mr. Rudd had said that there were some similarities to the character he played and his director, Mr. Hamburg rolled his eyes affectionately and sighed, “Oh, Rudd. O.K., let me say this: My wife and I have made a summer salad together and yes, we’ll hang out and watch a Top Chef marathon. What red-blooded American male doesn’t enjoy Project Runway and Top Chef? Pretty much my TV is always tuned to televised golf or Bravo.” He grinned. “And herein lies the complexity of John Hamburg.”