He's the heartbreaking, slick and stylish cad Don Draper on 'Mad Men,' but in today's Way Back When, we take a look back at Jon Hamm long before every woman was swooning over him.

'Space Cowboys'

One of Jon Hamm's first roles was the prestigious part of "Young Pilot #2" in 'Space Cowboys' -- that movie about really old guys being our last hope in space or something. Your grandpa knows it, ask him. In the clip below, Chris Wylde (forgot about him, didn't you?) approaches Hamm and another pilot buddy asking for a dangerous flight or something, and the gentlemen defer to Tommy Lee Jones, who is apparently a loose cannon and the only man for the job. We'd like to point out that this movie came out in 2000, and Jon Hamm hasn't aged in 12 years.

'Kissing Jessica Stein'

Hamm starred in this film, written and directed by his longtime girlfriend, Jennifer Westfeldt. 'Kissing Jessica Stein' is no embarrassment on Hamm's resume, that's for sure -- it's a quirky, cute indie comedy that hasn't aged much since it was released in 2001. Here Hamm plays Charles, a guy that Westfeldt's character thinks she's being set up with, but it turns out he's already found someone else.

'We Were Soldiers'

In 2002, Hamm pre-empted his role of soldier Dick Whitman/Don Draper in 'Mad Men' by starring alongside Mel Gibson in 'We Were Soldiers.' If we've learned anything from this clip, it's that they use a lot more phones in combat than we realized, and yelling at Mel Gibson makes him walk really funny. Oh hey, we solved the Mel Gibson anger mystery: please to be removing whatever inanimate object is shoved up his pooper.

'Gilmore Girls'

Hamm guest-starred on this season 3 episode of 'Gilmore Girls' as Peyton Sanders, a name which makes us think of a blonde-haired tennis player with tan calves and a righteous knit sweater tied about his shoulders, but this is close -- Hamm orders the last glass of Merlot at an auction (Don Draper would destroy him) and fights Lorelai Gilmore for it. And also: who let his hair be like that? WHO?! Poor form, 'Gilmore Girls' hair department.


It's hard to tell what Jon Hamm is doing in this episode of 'Charmed,' but something about a shipment and customs and booooooring. Let's talk about those sideburns! Unlike the subtly bad 'Gilmore Girls' hair, Hamm's hair here has a go big or go home vibe about it, and it's definitely eating more scenery than Rose McGowan.

'Ira & Abby'

Hamm joined the cast of girlfriend Jennifer Westfeldt's next film, 'Ira & Abby,' about a neurotic Jewish writer (Chris Messina, before he was famous!) who can't commit and the free-spirited woman he marries on a whim. But Abby (Westfeldt) has been divorced twice, and one of those ex-husbands is Jon Hamm. Chris Messina and Jon Hamm? This lady is the luckiest.