The Oprah Winfrey Show
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Vince Vaughn
When he made his first Oprah Show appearance in May 2006, actor Vince Vaughn opened up about his movie The Break-Up, his co-star Jennifer Aniston…and squashed tabloid rumors that Oprah was throwing Vince and Jen an $8 million wedding!

After the show ended, Vince got a bit more personal, taking questions from the audience. When one man asked Vince if he'd ever gone through a "geeky" phase, Vince confessed he did! "I've always felt geeky, in a way," Vince says. "I've never felt like I was super cool or anything like that."

During his visit, Vince also revealed one of his all-time favorite places. "Chicago has always been my favorite city," Vince says. "I think growing up outside of it I'm probably prejudiced that way. But I think really what makes the city the best [is that] the people are friendly."

And he isn't the only one who loves it here. Jennifer loves Chicago, too, Vince says.

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From the show Never Before Seen Oprah Outtakes