The gig kicked off Swift's publicity blitz for her new album, 1989, and before the Grammy-winning singer took to the stage, she joined show host Kimmel for a spot of reminiscing.
Talking about a time before Swift was famous, Kimmel remembered an occasion when she and her mom Andrea visited the show ten years ago.
"Taylor came to our show with her mom and her guitar, and somehow she got a hold of the guy who books the bands here, Scott Igoe, and she asked if she could play a song for him. And he said, 'No, you can't be in the greenroom, we serve alcohol here. You're too young. You have to go.' So he threw her out," Kimmel recalled. "He threw Taylor Swift out of our building!"
Swift made it clear there were no hard feelings. "All's well that ends well," she said. "I think of it like this: You probably would have gotten in more trouble with Jimmy had he wandered out and been like, 'Why is there this random 14-year-old tiny child sitting here with a guitar case? What's happening here?'"
The 24-year-old singer said she felt nervous about showcasing her new album to the crowd.
"I'm more confident about this album than I've been about any of the other ones, which is a really nice feeling," Swift said. "But it's almost like you're releasing this thing into the world that you spent two years with, and it's just been mine for two years and now it's everybody else's. You know, sending it off to college."
Swift then headed onto Kimmel's outdoor stage, telling the 15,000-strong audience she was in awe of them.
"I honestly, in my life, never thought that I would see Hollywood Boulevard filled with people as far as I can see, just to see us play a few songs," she said.
Watch the video above to see Swift's performance of "Shake It Off."