Chelsea Handler is big, bold, brash and fiercely funny. From her TV shows Chelsea Lately and After Lately, to her four best-selling books, sold-out live stand-up shows and most recently her movie roles, this notorious party girl has proven she is a serious Hollywood player. Katie kicked off the conversation by asking Chelsea’s about her latest project, her new book.

“I’m more conservative than one would think.”

Anyone who knows anything about Chelsea knows about her sidekick Chewy. What’s he been up to and how did they meet?

“Wouldn’t it be great if this guy could become famous?”

Although Chelsea admits she’s always had a sassy mouth on her, it was a very unlikely situation that launched her comedic career. Talk about turning lemons into lemonade!

“I just wish I could control myself!”

Next, a serious side of Chelsea we’ve never seen before. She’s joked a lot about her middle class New Jersey family, but today she really opened up about two tragic events that shaped her family life.

“You don’t ever recover from that.”

As the host of Chelsea Lately, Chelsea is just as used to asking the questions as Katie is. So Katie gave Chelsea the chance to turn the tables on her!

“I like that you’re always dating younger men!”

Although Chelsea revealed her more serious side today, she couldn’t help herself and had to play a joke on Katie before the show.

From sassy to sweet. We ended the show with Ron Fugelseth, his son Jayden, and the amazing video they made with Jayden’s favorite toy, a train named Stanley. The video of Stanley traveling to space was posted just a week ago and has been viewed over 2.6 million times.

“It all started with Jayden and his love for Stanley.”