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5 (Mostly) Forgotten Films with Ben Stiller

Born into a family of famous entertainers, Ben Stiller has been in the business for decades, acting, writing, and directing in many hugely popular films. With an edgy flare for comedy, he’s shown a lot of talent for drama as well. While best known for smash hits like There’s Something About Mary, The Focker films, and other comedies, there are a lot of great titles that have gone unseen by most. Here are 5 great (mostly) forgotten films with Ben Stiller.

Permanent Midnight (1998)

Ben Stiller

Stiller plays Jerry Stahl, a (real life) television comedy writer with a very expensive cocaine habit that is slowly eroding his world. He enters a program and meets survivor Kitty (Maria Bello) where he shares, in flashback, his life story leading to now. Based on the experiences of Stahl, drawn from his book of the same name, the film marks a departure in some sense for Stiller, who, to this point had established himself as a comedic actor. Directed by David Volez, the movie is well-cast and Stiller is surprisingly effective as a man consumed by an addiction that has led his life and career to disastrous ends. The plot is nothing new and there is little in terms of surprise, but Stiller keeps this above the line with an honest, intimate portrayal.

Keeping the Faith (2000)

Ben Stiller

Stiller plays Rabbi Jake Schram, the youngest rabbi in his synagogue, keeping his mother (Anne Bancroft) in distress while suffering through an endless line of woeful blind dates. His best friend since childhood is Brian Finn (Edward Norton) a Catholic priest with a heavy drinking problem. Back into town comes Anna Riley (Jenna Elfman), a girl they knew as kids but has now become a beautiful woman. The two men become attracted to her, but because she is not Jewish, Jake can’t think about a relationship with her if he wants to keep in good standing with his congregation, and since Brian isn’t allowed to marry, he is equally frustrated. When they both learn the other wants to be with Anna, their own friendship is tested. Directed by Norton, this unusual romantic comedy doesn’t try to be more than it suggests, but the chemistry among the leads keeps this fun to watch. Stiller, with his patented brand of neurotic charm, is especially on target.

Flirting with Disaster (1996)

Ben Stiller

Stiller plays Mel Coplin, a young husband with a new baby. He tells his wife Nancy (Patricia Arquette) that they can’t name the baby until he learns who his real parents are, having been adopted when he was an infant. The adoption agency tracks down his mother through the computer and the agent, named Tina (Téa Leoni), travels along with the couple. Trouble starts right away of course as Tina mixes up the family name and they end up in the wrong house. It gets worse when Tina, a sexy, leggy flirt, gets close with Mel. They then meet a gay couple (Richard Jenkins and Josh Brolin), who are also ATF agents who follow along. A wicked black comedy with lots of sharp humor one unexpected twist after another, there is a lot to like about this movie. Directed by David O’Russell, with a cast that includes Mary Tyler Moore and Alan Alda, it’s a real gem that flew under radars and was misunderstood by audiences. Funnier now than on release, this is one to watch.

Greenberg (2010)

Ben Stiller

Stiller plays Roger Greenberg, a former musician who walked away from potential fame, abandoning his bandmates and moving to New York to be a carpenter, never giving a reason why. Now, years later, he returns to L.A. to look after his wealthy brother’s very large house and his pet dog. Lost in the house, he contacts Florence (Greta Gerwig), his brother’s assistant, who knows where everything is, and the two begin a rather interesting relationship. Directed by Noah Baumbach, whose The Squid and the Whale is also a minor masterpiece, Greenberg is a deliciously unconventional experience that sees Stiller in a role that is tailor-made, so perfectly crafted and executed, it feels like a snapshot of a real life. It is easily the best performance of his career.

Zero Effect (1998)

Ben Stiller

Stiller plays Steve Arlo, an exasperated assistant for a hermit detective of unparalleled deductive powers named Daryl Zero (Bill Pullman). Arlo acts as a representative, a figurehead and liaison for Zero who has an uncanny sense for human behavior, even though he rarely sees any people. What sounds like a comedy is anything but, despite some very funny moments. Directed by Jake Kasdan, the plot of Zero Effect is worth the price of admission alone, but it is Stiller’s performance, and his character’s relationship with the clearly off-kilter genius of his boss, that make this so special. While Stiller’s best role is Greenberg, as mentioned above, this film is without a doubt, the best on the list, and arguably of his career. A caper, a comedy, a dark, drama, and an intense examination on the human condition, this movie satisfies from start to finish.

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