It was 1996 — David Letterman was still going strong as the host of "The Late Show," and the nation was awash in choker-clad Gen-Xers, who collectively took a break from grunge to learn the Macarena. As per Biography, Jennifer Garner had just nabbed a small guest role on "Spin City," a sitcom starring Michael J. Fox and Heather Locklear. As it turned out, Stephen Colbert had landed a guest role on the same episode of the show — although, it looks like Garner was the bigger star at the time, as she recounted having a total of 10 lines, while Colbert had only two.

The two relative unknowns struck up a conversation during the episode's wrap party, something they would reminisce about two decades later when Garner appeared on an episode of "The Late Show With Stephen Colbert" to discuss an upcoming project. "You said, 'Well, I'm out of a job,' and I said, 'I'm out of a job too, and I have a baby," Colbert recalled, to which Garner interjected: "I babysit!". And just like that, the young actor had landed one of her first jobs: babysitting Colbert's young daughter, Madeline, in between her shifts waiting tables at a restaurant.

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