I Want Someone to Eat Cheese With is an indie film from 2006, released in September 2007 by IFC Films and The Weinstein Company. Written and directed by Jeff Garlin (of Curb Your Enthusiasm), it features Garlin, Sarah Silverman and Bonnie Hunt. Many improv veterans of Chicago's Second City and even its 1950s predecessor Compass Players appear, as well as Chicago radio personality Steve Dahl in a cameo.

Overweight, depressed improv actor James (Jeff Garlin) is a Second City cast member in Chicago. He lives with his mother (Mina Kolb, who also plays Garlin's mother in Curb Your Enthusiasm), and cheats on his diet. He quits his acting job on a sleazy television prank show, his girlfriend (Rebecca Sage Allen) breaks up with him, and his agent (Richard Kind) dumps him. When he visits his friend's daughter's elementary school for Career Day, he rambles about his problems, boring the kids, and embarrassing himself in front of the teacher, Stella (Bonnie Hunt). James relaxes in the evenings by lying on the hood of his car parked "in a great spot" beside Wrigley Field, and during the days by walking around the North Side of Chicago with his friend Luca (David Pasquesi), appreciating the buildings.

While wearing a pirate costume for a hot dog stand, James hears about a Chicago-based remake of Paddy Chayefsky's 1955 Marty, his favorite movie, and one that mirrors his adult life. He knows the director but cannot get an audition.

After walking out on his Compulsive Eaters Anonymous meeting, James goes to an ice cream parlor, where he meets "big-time hottie" Beth (Sarah Silverman), who recognizes him from Second City and offers him free ice cream. She asks him an obscurely lewd question, which she then cheerfully explains to him. When James, smitten, returns to the shop, Beth takes him on adventures, including a shopping trip for her to try on underwear. She disposes of him after "seeing what it was like to be with a fat guy." Meanwhile his role in Marty is given to a clueless young actor, real-life teen idol Aaron Carter.

As the story ends, James moves to his own apartment and reconnects with Stella, the elementary school teacher.

"Garlin struggled to find financing, which twice fell through. He shot it in 18 days, but those days were spread out over two years," reported the Associated Press.

IFC Films released the film on a non-traditional schedule, called "IFC First Take", part of IFC in Theaters. It appeared on pay-per-view cable television simultaneously with a limited theatrical release, in September 2007. The DVD would follow about seven months later, April 15, 2008. But in the meantime, IFC Films made a deal with Blockbuster, giving the video chain 60 days of exclusive rental and Video on Demand rights on each film. So as of March 2008, the DVD is available to rent at Blockbuster.

During interviews on Late Night with Conan O'Brien and Wait Wait... Don't Tell Me!, Jeff Garlin said that the title bothers Larry David because it ends in a preposition.

Rotten Tomatoes gave I Want Someone to Eat Cheese With a "fresh" rating of 74 percent with 34 positive reviews and 12 negative ones, with the "cream of the crop" giving it a rating of 81 percent. The New York Times calling the "rambling" film "laid back and affectionate". In a appreciative review, Chicago-based Roger Ebert called it "a minor movie, but a big-time minor movie... If there is such a thing as a must-see three-star movie, here it is." But John Maynard in The Washington Post scorned the movie, writing, "A better awkward title would be 'Random Events of a Failed Actor Plodding the Streets of Chicago.'"