The singer also talks about the surreal experience of having Chuck Norris as her acting coach and the weirdest advice he gave her at 12 years old.
Jessica Simpson's "Open Book" is filled with very serious and heartbreaking stories from throughout her life, but Jimmy Kimmel opened up to some of the lighter fare in it when he had the singer on his show Wednesday night.
After her breakthrough into pop culture as a singer alongside the likes of Britney Spears, Justin Timberlake and Christina Aguilera, Jessica became known for her innocence about the world around her, cracking a whole new group of fans up with her reality series "Newlyweds" with then husband Nick Lachey.
She brought all of that charm and laughter with her to this more lighthearted chat where she talked about almost making it onto that murderers' row of talent on "The Mickey Mouse Club" with Aguilera, Spears, Timberlake and Ryan Gosling.
"I did go to the finals but they said that I needed acting lessons," Jessica explained, which is how she found herself attending an acting school run by Chuck Norris in 1992, which precedes by about a year his "Walker, Texas Ranger" era.
When Jessica started talking about what she learned, Jimmy had to stop her. "I don't want to just slide by Chuck Norris being your acting coach," he said.
"And Barney was my acting partner," she said. And yes, she was referring to the big, purple dinosaur. If this wasn't her life, it would be totally unbelievable!
Simpson did enjoy a modest film career, highlighted by a co-starring role as Daisy in the 2005 remake of "The Dukes of Hazzard." Her eyebrows were under control the whole time.
While she never made it on to "The Mickey Mouse Club," Jessica nevertheless maintained friendly relationships with several of those who did, and even revealed that things once got intimate with Justin Timberlake ... though it wasn't at all how she imagined.
It went down after her divorce from Nick Lachey and while Justin was single. "He was like over at my house and we shared a nostalgic kiss," she said sweetly. But then things took a strange turn.
"He took his phone out and started typing. I was like, okay, I hope that's not like another girl," Jessica said. "Did I stick my tongue out too much?"
But it was nothing like that. In fact, it was even more awkward, and a little disturbing. "Apparently him and Ryan Gosling had a bet on who would kiss me first when they were 12 years old, and so he texted Ryan and told him he won the bet," Jessica said. "And I was like, oh, okay? So we don't kiss again?"
And Jessica would actually have liked Ryan to win that bet, if it had been up to her or if she'd known about it. "Ryan was the one that when I was 12, I was like, this guy is so cool. He's from Canada; I don't know where that is on the map, but I really think that that's amazing and there's something so cute about him."
While most of the bombshell revelations from Jessica's book have been incredibly serious and in some cases disturbing and tragic, she shared with Kimmel that the book can go from making readers cry to having them laugh out loud with stories like the ones she shared with him.
You can check out some of the more serious stories from "Open Book" below: