Drew Barrymore on Bringing 'Hopefulness' Back to TV With Talk Show's Star-Studded Season 2 (Exclusive)

Jennifer Aniston, Billie Eilish and Cameron Diaz are among the show's slated guests!

The Drew Barrymore Show's sophomore season is starting out with a bang! CBS Media Ventures announced on Tuesday that the Drew Barrymore-hosted series will kick off a two-week-long premiere event on Sept. 13 with some A-list talent including Jennifer Aniston, Billie Eilish and more.

When ET's Kevin Frazier spoke to the 46-year-old host, she couldn't contain her excitement about welcoming Jennifer Aniston as her first guest of season 2.

"We're gonna launch with none other than someone who might be one of my favorite people on planet earth, Jennifer Aniston," Barrymore exclaimed. "... I'm so excited, because that is a movie star, an entertainer, a woman, a human, someone that we just all marvel at. She has longevity. I love this woman so much. I can not believe I'm gonna get to do this with her."

"I can't think of anyone who I would rather listen to than her. I just find her to be such an extraordinary woman that garners our attention and has for so long," she added. "... It's anyone's dream to have her be that first guest. Any guest whatsoever. If Jennifer Aniston will come play in your field, you know it's the best day ever. I hope to give her an afternoon that she walks away from feeling like, 'That was different. I feel great about this. I was myself.'"

After Aniston begins the show's premiere week, the second episode will feature Molly Shannon, David Arquette and Michael Vartan for a Never Been Kissed reunion.

"The whole crew is coming back and we are gonna do not just a reunion. It will be something a little more intricate," Barrymore told ET of reuniting the cast of the 1999 rom com in which she starred.

The reunion won't be the only nod to Never Been Kissed in the show's sophomore season. In fact, Barrymore plans to return to her role of reporter Josie Grossie by sending her to movie junkets to interview people.


"Stepping back into Josie Groosie's shoes is so easy. I don’t think I have ever not been in her shoes. I loved this character so much. She was so personal for me," Barrymore said. "This whole story for me was not to do another rom com, it was to embody a human being that represents us all. How and when do we become OK with ourselves? That is what Never Been Kissed is all about."

"That is why Josie is really excited. She is really earnest, too," she added. "She's got big feelings and understands big feelings, and I think we can all understand and relate to the fact that we have a lot of big feelings in the world today."

Also on the second episode of the season, Barrymore will be joined by RuPaul as they embark on a new journey together and head back to school to get their high school diploma equivalent. It's one example of how Barrymore will revisit her past this season.

"I am basically getting an old blue Bronco that I used to drive when I was 16 years old, and I am going to go and visit all of the places I grew up," she told ET. "I am going to swing by my first apartment when I was 14, the bizarre little duplex I grew up in. I am going to swing by the weird little institution that my mom put me in. I am going to go to the Chinese Theater and put my face in my father's profile that is in the cement. I am going to go to my old schools that I didn’t really attend because I was mostly on movie sets."

"I really want to have [it be] authentic," Barrymore continued. "... It doesn’t matter if you think you know somebody, you probably don't know what their lives looked like, especially because people didn’t see the way I grew up that wasn’t in front of the camera... When you can look back and know where you are now is a place you are happy with, that's kind of an awesome journey."


The third episode of season two will feature Cameron Diaz, Barrymore's longtime friend.

"My bestie is coming back. We're gonna do a Besties Hour, which is gonna be so exciting," Barrymore said. "... She happens to be my bestie. She's probably my only famous bestie."

"We became friends when we were 14 and 16, so it wasn't Charlie's Angels," she revealed to ET on Wednesday. "I worked in a coffee house, I was the barista. I sucked at my job and my boss hated me ... she came in and she was a junior model and I just fell in love with her because she was so pretty but so goofy and cool." 

The next day Eilish will join the fun, something Barrymore's eagerly awaiting.

"I have butterflies in my stomach [over] how excited I am [to talk to her]. As someone who grew up in front of everybody, I am more fascinated by her than most people, because she has a real conviction and strength," Barrymore explained. "I look forward to seeing her grow up, evolve. To possess what she does at her age and to have the opinion she has, the upbringing of her family in a unique way, she is a real dichotomy, and her talent is limitless."

"I think she has some very rare strengths," the host added of Eilish. "I'm curious as to if she'll give herself the room to change and grow, 'cause you do so much when you grow up, but I feel like she's working from cylinders that are really abnormally amazing."

A special Emmys Hour, co-hosted by ET's Nischelle Turner and Kevin Frazier, and featuring Cedric the Entertainer, will round out the week.

"I think award shows have got to evolve into something different. I think they're a little archaic right now and we don't need pageantry and contests in the world we're living in," Barrymore said. "We do need to celebrate the art of entertainment, 'cause as much as I even question what any of us are doing in the pandemic, I came back to the fact that there is merit in this. That we do need education, entertainment, escapism, information, pop culture, all the goods."

The following week, Barrymore will welcome guests including Awkwafina, Carmelo Anthony, Ziwe Fumudoh, Ben Platt, Amy Adams, Julianne Moore and Martha Stewart

"I don't have an agenda other than to try and get everyone else to feel as comfortable as possible. Let this be a conversation, it's never going to be an interrogation. I don't want to just keep it on the surface 'cause that's so boring," Barrymore said of her interview style. "... I want to push the envelope, but I have no interest in upsetting people. That really is not who I am. It's so against who I am. So that weird line is a weird one to tread all the time, but I love it."

As she heads into season 2, Barrymore said her show is all about finding "balance."

"The thing about a show like this for me is to find the balance of the art of conversation with the people you know and love, to meet the people you have never heard of and now cannot get out of your mind and are inspired by," she said. "The food, the design and the news... but also, how do we engage and do a little variety?"

"I came from the era of television where there was a lot of playfulness. There have been so many talk show hosts that have carried that torch continually. That was always the art of how to bring that to daytime. This season is a really great opportunity for us to keep going with that," Barrymore continued. "... I also think that this is a time where we can get back to some of that sweetness that television had. There was a gentleness and hopefulness that I think we need back."

Season 2 of The Drew Barrymore Show will premiere Sept. 13.