Britney Spears' debut film 'Crossroads' is 21 years old — here are the best photos from the red-carpet premiere

Esme MazzeoJan 13, 2024, 19:06 IST

Taryn Manning, Britney Spears, Anson Mount, and Zoe Saldana posed together.Steve Granitz/ SGranitz/WireImage

"Crossroads" premiered at Grauman's Chinese Theatre in Hollywood, California on February 11, 2002.
Justin Timberlake and Britney Spears made one of their final appearances as a couple at the event.

In honor of Britney Spears' upcoming memoir, her debut film "Crossroads" is returning to theaters.

Insider dove into the photo archives to take a look back at the stars who came out for the 2002 release of the movie. Here are the best photos from the event.

Britney Spears was pretty in a casual pink outfit, perhaps inspired by her "Crossroads" character Lucy.

Spears played an aspiring singer in the film, which was written by Shonda Rhimes.Jeff Kravitz/FilmMagic

Spears' then-boyfriend, *NSYNC member Justin Timberlake, was by her side.

Spears and Timberlake hit the carpet together at the premiere of' "Crossroads."Kevin Winter/Getty Images

The pair were in a playful mood on the night that would mark one of their last public appearances together.

The 2002 event happened near the end of their relationship.Jeff Kravitz

Of course, Spears' co-stars Taryn Manning, Anson Mount, and Zoe Saldana were in attendance too.

Taryn Manning, Britney Spears, Anson Mount, and Zoe Saldana posed together.Steve Granitz/ SGranitz/WireImage

Manning played Lucy's pregnant friend, Mimi, while Mount played Lucy's love interest, Ben.

Taryn Manning, Britney Spears, and Anson Mount posed together on the red carpet.Jeff Kravitz/FilmMagic

Saldana played Lucy and Mimi's childhood friend, Kit.

Zoe Saldana gives cameras a wave at the "Crossroads" premiere.Jeff Kravitz/FilmMagic

The leading ladies posed with other attendees, like the film's director Tamra Davis.

Tamra Davis and Taryn Manning at the premiere of "Crossroads" in Los Angeles.Kevin Winter/Getty Images

It also won't surprise Spears fans that Sabrina the Teenage Witch herself, Melissa Joan Hart, made an appearance to support Spears. The two had worked together before.

Melissa Joan Hart in an extremely 2000s shirt at the "Crossroads" premiere.Steve Granitz/WireImage

Hilary Duff, then only 14 years old, showed up looking like a shining star fresh off of "Lizzie McGuire" fame.

Hilary Duff in lots of denim at the "Crossroads" premiere.Steve Granitz/WireImage)

Tracee Ellis Ross' hit sitcom "Girlfriends" was in its prime in 2002.

Tracee Ellis Ross at the "Crossroads" premiere in LA.Steve Granitz/WireImage

At the time she stepped onto the carpet for the "Crossroads" premiere, Christina Milian had a hit song on the radio with "AM to PM."

Christina Milian at the "Crossroads" premiere in Los Angeles.Steve Granitz/WireImage

Nick Cannon made an appearance too, years before he welcomed the first of his 12 kids.

Nick Cannon at the "Crossroads" premiere.Steve Granitz/WireImage

It turns out designer Roberto Cavalli was down for a chick flick in 2002.

Roberto Cavalli during "Crossroads'" Hollywood Premiere at Grauman's Chinese Theatre.Ron Galella, Ltd./Ron Galella Collection via Getty Images

So was Angelina Jolie's dad, Jon Voight.

Jon Voight at the "Crossroads" premiere.Steve Granitz/WireImage.

Heather Matarazzo, fresh off of 2001's "The Princess Diaries," flashed a big smile on the red carpet.

Heather Matarazzo during "Crossroads" Hollywood Premiere at Grauman's Chinese Theatre in Hollywood.Steve Granitz/WireImage

Here's a young Mae Whitman, then starring on the ABC Family comedy-drama "State of Grace," a year before her breakout role in "Arrested Development."

Mae Whitman at the "Crrossroads" premiere.Steve Granitz/WireImage

And here's baby-faced 12-year-old Brie Larson, years before she'd become Captain Marvel.

Brie Larson at the "Crossroads" premiere.Steve Granitz/WireImage

We'll leave you with a final look at Spears basking in her leading lady glory, not long after she doodled Timberlake's name in hearts on her "Crossroads" set notebook.

Timberlake and Spears coupled up in 2002.Gregg DeGuire/WireImage

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Britney Spears' debut film 'Crossroads' is 21 years old &mdash; here are the best photos from the red-carpet premiere