'Drive Me Crazy,' featuring Melissa Joan Hart and Adrian Grenier, was first released on Oct. 1, 1999.
It's hard to believe it's been two decades since the release of Drive Me Crazy!
The popular '90s movie, about two friends who staged a relationship to get back at their exes, was released on Oct. 1, 1999. In celebration of its 20th anniversary, ET spoke with Melissa Joan Hart, who shared a series of interesting (and intimate!) behind-the-scenes secrets.
Recalling that time in her life, Hart (who portrayed Nicole Maris opposite Adrian Grenier as Chase Hammond) remembered it being "so much fun."
"It was such a big cast of so many people my age," she told ET's Katie Krause at the junket for her new Lifetime movie, Christmas Reservations. "Anytime I get to work with peers, it's awesome, especially in that movie. We were shooting in Utah, I had the role of Nicole, but we were trying to find who was going to play Chase, so [Adrian and I] did a screen test together."
"I was just thinking This guy is good, like, he's deep and he's going to push me to be better, I don't know if I want to work with him," she continued. "I was working with an acting coach and he and I were running the scenes together constantly and just really taking my craft seriously for the first time I feel like. Just having those kids around and being able to play in Utah a little bit, just having fun on the set, everybody was hooking up with everybody."
Hart said she and Grenier never hooked up, but they did have a little fun with some other people on set.
"Adrian and Ali Larter," she revealed. "And me and a guy named Gabriel Carpenter who played [Brad] the boy I was chasing in the movie. The very tall guy, yes. I have a thing for very tall men."
Another unforgettable moment? Working with Britney Spears! Hart was featured in the pop star's music video for "Drive Me Crazy" at the time, and it's an experience she'll remember forever.
"She and I were crossing paths a lot at the time," Hart recalled. "She came and did a bit on Sabrina and because of the movie, we had to do a lot of press together. We hosted TRL together, so there was a lot of us meeting up in random states around the country at random events."
"But also with *NSYNC and Backstreet Boys and all those people at the time, it was always fun to run into friendly faces and she and I became friendly," Hart continued. "We had a little bit of an age difference and I was always trying to break her out of... she was very protected by a lot of people and I was always trying to be like, 'You need to let loose, you're, like, 17. You need to not always be, like, in the gym, working, doing your Pepsi commercials. Like, let's go out and go dancing.'"
Hart, now 43, is married to Mark Wilkerson and the two share three kids -- Tucker, Mason and Braydon -- together. Spears, 37, is also a mom to sons Sean and Jayden, whom she shares with ex-husband Kevin Federline.
Hart said that she and Spears "haven't really kept in touch in decades," but she did support the singer at one of her residency shows in Las Vegas a few years ago.
"We got to meet up there," she remembered. "We are both moms now and we are in a new stage of our careers. I wish we had gotten time to just sit and talk, but it was all kind of real quick. She was going onstage, you know?"
"I would love to catch up with her, but we just have these busy, different lives," she added.
For her part, Hart is currently busy gearing up for the premiere of Christmas Reservations, which airs Nov. 2 at 8 p.m. ET/PT on Lifetime. She says the best part of shooting this movie was the fact that it felt like Christmas "all year round."
"We shot this one in May. We actually filmed in Tahoe, where I live right now, so it was awesome because we had snow until June," she shared. "It actually snowed a few days on set so it was kind of awesome. We got to build snowmen and drink cocoa by the fire and we had a dog in this one."
"We had a fantastic cast," she continued. "Such fun people to play with."