The capacity to fall deeply, madly in love is fundamental to humanity. As is the inevitability of having our hearts painfully, inextricably torn apart. But in the darkest of places, there is the funniest of comedy.
Judd Apatow and Jason Segel have this shared history of dark humor. The longtime friends first worked together in 1999 on the Apatow-created television cult classic Freaks and Geeks, in which Segel played confused 1980s McInley High student Nick, and again in 2001, as underclassman Eric in Apatow's short-lived, but critically acclaimed television show Undeclared. In 2007, they teamed with producer Robertson on the box-office hit Knocked Up-in which Segel received acclaim by portraying one of the juvenile, yet lovable, best friends of lead Seth Rogen as slacker Ben Stone.
Several years ago, Segel had discussed with the filmmaker his interest in writing and starring in a comedy about brutal heartbreak caused by a woman who had crushed a hopeful romantic's spirit and abandoned their future. Segel believed there was comedy to be found in not only a couple's time together, but in stories of the many bad things that happen after a relationship conceivably ends. Says Segel, "I had to cut my first draft down to 120 pages, because originally it was 2,000."
During a courtside conversation at a Lakers game, Segel told Apatow the idea. Apatow provided Segel with direction and guidance, and the first-time screenwriter moved forward with drafting a screenplay. Segel recounts, "Judd said to me, 'If you can improv the way you do, then you can also write.' And here we are making a movie together."
While obviously impressed enough by the actor's past performances to keep hiring him, Apatow admits he was surprised when Segel handed him a finished script and asked him for his notes. He recalls: "Jason went away to Hawaii, and he actually wrote a hilarious script. From the get-go, everyone was shocked at just how good it was. He is just so funny as a guy desperately in love, jealous and insane."
Apatow's producing partner on the company's hits The 40-Year-Old Virgin, Knocked Up and Superbad, Shauna Robertson, was equally impressed with the work of the first-time screenwriter. She recounts, "Jason's quite a prolific writer. We were really excited about the script." The producer jokingly adds, "I said, 'If you can come up with a movie where I can wear flip-flops all the time, I'm in.' So Judd said, 'Pack your bags, you're going to Hawaii.'"
During the time Segel was polishing copy, Apatow's writing partner on Fun With Dick and Jane (and a former staff writer on Undeclared), Nicholas Stoller, was searching for a script with which he could make his feature film directorial debut. Stoller was given a copy of Forgetting Sarah Marshall and was impressed enough by the draft to work with Segel over the course of a year and a half. The pair developed the story about a couple who had everything, until she decides to leave...and he blames her for everything.
Provides Apatow: "Nick and Jason get along great and share the same sense of humor. They had both been destroyed by women in the past, which is helpful. Actually, that has been a requirement for everyone who works on the movie. People who have had their hearts trampled on understand the material."
Surprised at being given the opportunity to have a movie made from his first attempt at a full screenplay, Segel laughs, "Somehow, Universal gave us millions of dollars to make this film and to exorcise my demons from bad relationships."
Director Stoller felt lucky to be guided by producers with a reputation for eliciting humor and deep emotions from the raunchy side. He was, however, pleased that the script didn't delve into his past demons, stating, "How wonderful that we didn't have to edit my breakup stories, as well as Judd, Shauna, Jason and [executive producer] Rodney's."
With a screenplay that the producers, the director and leading man were comfortable with, it was time to find a cast of characters that could wreak havoc on a tropical island. For the task, the filmmakers would turn to a former teenage P.I., a '70s stoner and a British shock jock...as well as some tried and true Apatow players.