Lexi Underwood embraces the Y2K aesthetic for Season Two of ‘Cruel Summer’

Underwood, 19, plays a teenager in 1999 in the second season of the anthology series.

Lexi Underwood gets to experience the height of the Y2K era in the second season of Freeform’s anthology series “Cruel Summer.”


Set in 1999 in a small Pacific Northwest town, Underwood plays teenager Isabella LaRue, a foreign exchange student who moves in with Megan Landry (Sadie Stanley) and her mother. The two teens become best buds until a tragic accident takes the life of one of their friends.


Speaking to, Underwood, who was born in 2003, says transporting herself to a time before she was born wasn’t all that strange because of the Y2K era’s influence on today’s culture.


“It was all pretty normal to me, especially because a lot of those trends and things about the Y2K that we love are coming back now,” she says. “I feel like you can’t, like, go on TikTok without scrolling past a video that has something to do with Y2K.”

Some of the those trends, according to The Trend Spotter, include metallic prints and jackets, chunky sneakers, wide-leg jeans, pleated skirts, cargo shorts, baby tees and velour tracksuits. Underwood says she still embraces most of those fashion trends in her daily style — except for one.


“I’m a big fan of everything that took place during the ’90s except for like cargo shorts,” she says, with a laugh.


“I would say that that’s probably like a major ‘No,'” she notes, before adding that plaid shorts are also “a little stupid.”


Although Underwood admits she “didn’t get to experience everything,” from that time, the “Cruel Summer” star says playing a character from that era felt very familiar.


“There are some things that I do remember — and then also just doing shows, like ‘Little Fires Everywhere’ — I knew a little bit about the ’90s and news-wise what was happening in the world at that time,” she says. “So it wasn’t hard to kind of immerse myself back into that time zone.”


To allow herself to get fully acclimated, the young star, who navigated playing her character in different timelines over the course of a year — from 1999 to 2000 — says she created the perfect strategy to help her stay on track.


“A big thing that came in clutch for me was using music as a tool,” Underwood says. “I made three separate playlists. I made a playlist for summer ‘99 Isabella, winter ‘99 Isabella and then summer 2000 Isabella. And so all three different playlists reflected how Isabella was feeling internally during those moments and so being able to listen to like, the top 10 or the top, you know, 50 songs during that time.”


Now, looking back to that era, the actor says that there are many things about the ’90s and early aughts she’d love to see return.

“I would say number one, I just love the lack of technology during that time,” she says. “I wish we could go back to like that place as a society where we’re not like obsessed with social media, obsessed with the Internet.”


Another thing that she wouldn’t mind seeing return: ’90s boy bands.


“My boy band crush during that time… I would say maybe somebody from like 112, or I really love Backstreet Boys,” she reveals. “I think that they’re dope. So maybe somebody from the Backstreet Boys, too.”


But on further reflection — and a quick reminder that NYSNC’s Justin Timberlake is the husband of “Cruel Summer” executive producer Jessica Biel — Underwood says she also has “love” for NSYNC, but could see herself counted as one of the Backstreet Army.


While there’s plenty of Y2K fashion, music and culture to relish in, Underwood says there’s one thing she’d glad is officially left in the past.


“I think that the whole thinking that the world was gonna end it’s a little dumb,” she quips. “I think — I don’t know — if I was alive during that time I wouldn’t necessarily think that the world was gonna end, but I also do understand why maybe people thought that way because people didn’t know what’s gonna happen.”


Still, if there’s one thing that’s for sure, Underwood says those who tune will definitely find something that they can relate to, whether they lived in Y2K era or not.


“I think that what’s so beautiful about the show is that like all generations, you know, they can relate to it,” she says. “Because these characters are all very authentic. And I feel like somebody can find at least one character that they can relate to… like, ‘Oh, that’s how I was when I was younger,’ or ‘Oh, that’s how I am now.'”


“Cruel Summer” Season Two premieres June 5 on Freeform.

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