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In the first episode, Steven rips up his X-Files poster, ditches his dorky pals, tries to slide by as a cool guy in cool clothes he wears as comfortably as if they were lined with bees and sleeps with the girl across the hall, Lizzie (Carla Gallo). But Steven discovers early on he can't quite leave home: His father, played by wry singer-songwriter Loudon Wainwright III, shows up during a first-night dorm party to break the news of his imminent divorce from Steven's mother. Wainwright becomes a rather permanent fixture on the show; he, too, is newly liberated and longing to remake himself in the rather uncomfortable image of a drunken, porn-collecting swinger. Steven spends the first season trying to reconcile his love for his father with his embarrassment for the old man, who can't hold a job and a beer bong at the same time.
Steven also has to cope with dorm mates he can't decide whether he likes or loathes. His roommate is a ladies'-man Brit drama student, Lloyd (Charlie Hunnam), who looks suspiciously like Heath Ledger; they share a suite with the laconic music major Marshall (Timm Sharp) and the sarcastic, easily outraged business major Ron (Freak's Rogen, a 19-year-old former stand-up comic who pens many of Undeclared's stories). And theirs is not a great friendship: These four kids are pals by accident, forced to share living quarters and sort out their differences without really knowing each other. In subsequent episodes, they find they have little tolerance for each other; Steven even abandons the group for a while to pledge a frat.
"Paul [Feig] and I think of ourselves as being a lot like Sam--well, as most of the characters on Freaks and Geeks--which is a sweet kid who's trying to survive high school and has an interest in comedy and isn't getting treated very well but in his heart is a really good guy," says Apatow. "And then Steven is a very similar type of character, but that's how I perceive myself. When I was in high school I thought, “This isn't my time.' When I got to college I thought, “Now is my time,' and I really tried hard to show up at college and present myself differently, as someone who might get a girl and might be popular and take the lead in situations. I failed miserably immediately...
"To me, a lot of what the show's about is this kid going to school trying to start his life at the same time his dad's life has fallen apart, and he's forced to deal with his dad's failures while he's trying to get a good leg up on his hopeful success...And Steven's taking way more shit than anybody, which is something that would always happen to me. No matter who I was with, after three weeks everyone was making fun of me."
But Apatow's is, in the end, the story of the geek whose ambition trumped his self-professed shortcomings. The Syosset, New York, native wanted to be a stand-up comic the moment his parents were divorced; a scene from Freaks and Geeks, in which gangly Bill Haverchuck, played by Martin Starr, comes home and flips on The Dinah Shore Show to watch Garry Shandling is lifted directly from his own experience. He attended the University of Southern California's film school, but stayed only two years and one month, or until the money for tuition ran out. Besides, he wanted to stand in front of a comedy club's brick wall and tell jokes, and before long, he was a stand-up who made spare scratch providing jokes for the likes of Shandling and Jim Carrey and Roseanne Arnold.
His first job in television was on another short-lived series, The Ben Stiller Show, which he co-created for Fox; it lasted 12 episodes during the 1992-'93 season but garnered an Emmy for its writing. In 1993, he took his shiny statue over to HBO, where he landed on the writing staff of Shandling's The Larry Sanders Show. During its final season, he had been promoted to co-executive producer, and he would go on to work on The Critic and a handful of films, among them Carrey's Liar, Liar and The Wedding Singer with Adam Sandler (who appears in a later episode of Undeclared, as himself).
"You know, while making Undeclared, I didn't think it was very personal to me, because I didn't spend a lot of time at college," Apatow says. "While I was at college, I was obsessed with being the next Jay Leno or Jerry Seinfeld. But the more I look at the episodes now with a little distance, I begin to see that they're incredibly personal to my experience of my family, to my experiences with my long-distance girlfriend, and to my experience of going to college and being surrounded by all these good-looking people who seemed more confident and at ease with this experience. So I guess it is personal, and I must be rewriting my experience, because Steven does get the girl his first night, and I never did." He laughs. "That's the geek's fantasy, but a lot of what I do is about the geek's fantasy."
Correction: This article says Paul Feig and Judd Apatow were co-creators of Freaks and Geeks. Actually, Feig was the show's sole creator, and Apatow was executive producer.