Jason Segel caught our attention playing lovable goofs with roles on 'How I Met Your Mother' and in Judd Apatow's 'Knocked Up,' but in today's Way Back When, we take a look at one of our favorite actors before he became someone to watch.

'Can't Hardly Wait'

Segel's first role was in the high school graduation night comedy 'Can't Hardly Wait' in 1998, as "Watermelon Guy." For fans of 'Freaks and Geeks,' his role here is a precursor of sorts, since his character is a stoner and spends the whole movie engaged in dumb conversations, like the one in the clip below, about how sexy Velma from 'Scooby-Doo' is:

'Dead Man on Campus' (Language NSFW)

This oft-forgotten film produced by MTV starred Mark Paul-Gosselaar and Tom Everett Scott as college buddies who have found a loophole to ensure they get passing grades: if they have a roommate that commits suicide, the dean will have to pass them in all of their classes. The two set about trying to find the perfect roomie to manipulate into killing himself (yeah, it's pretty dark), including a young Jason Segel playing a meathead. And in another 'Freaks and Geeks' connection, Linda Cardellini plays the girl of his dreams:

'SLC Punk!'

This 1998 indie flick told the story of two modern punks (Matthew Lillard and Michael A. Goorjian) living in Salt Lake City, Utah. Segel played one of their friends, Mike -- a nerdy-looking and soft-spoken dude who happens to have a surprising and awesome hardcore streak. Watch Mike's introduction below:

In this scene (a bit lower in quality), Mike explains that he's going off to college, which his friends find very conformist, but hey, he wants to study botany and save the rainforest!

'Freaks and Geeks'

Segel starred on the short-lived Paul Feig series 'Freaks and Geeks' as Nick Andopolis, a stoner obsessed with playing the drums and bands like Styx and Rush (not too far off from his part in 'I Love You, Man'). In the scene below, he tries to convey his feelings to girlfriend Lindsay Weir (Linda Cardellini) through the Styx song, "Lady." It's super corny, but too cute:


In this underrated comedy, Segel stars with Devon Sawa, Jason Schwartzman (before he fixed his eyebrows) and Michael C. Maronna (Big Pete from 'The Adventures of Pete and Pete'!). The guys star as -- what else -- slackers who are scamming on their exams, until Schwartzman's creepy character uncovers their plot and uses it as blackmail to date a popular girl. In the clip below, Segel fantasizes about treating women poorly, and his daydream features a cameo by Gina Gershon:


Paul Feig followed up 'Freaks and Geeks' with another tragically short-lived and under-appreciated series, 'Undeclared.' Segel joined Jay Baruchel, Charlie Hunnam, Seth Rogen, Monica Keena and Carla Gallo in this sitcom about college freshmen. Segel's character, Eric, was dating Gallo's character, Lizzy, and the pair had a really codependent thing going on; but when Lizzy dumps Eric, he completely loses his mind -- in the most hilariously heartbreaking way: