‘Crossroads’ Cast Transformations: See Britney Spears & More Then & Now After 19 Years

If you’re a fan of Britney Spears, then you love ‘Crossroads.’ The movie came out 19 years ago today, so take a look back at Brit and more of the cast’s transformations over the years.

Britney Spears was already one of the biggest pop stars in the world when she decided to star in her very first movie, Crossroads. In the film, Brit showcased her acting skills as well as her incredible vocals. Crossroads was written by Shonda Rhimes, who went on to create Grey’s Anatomy just a few years later.

Crossroads was released on Feb. 15, 2002. Despite not getting the best reviews, the movie earned more than $60 million at the box office. Britney had a solid supporting cast, who are all still working together. See the cast of Crossroads then and now in honor of the 19th anniversary.

Britney Spears

Britney Spears then and now. (Everett Collection/AP)

Britney Spears, 39, made her feature film debut in Crossroads as Lucy Wagner. She recorded multiple songs for the movie’s soundtrack, including “I’m Not A Girl, Not Yet A Woman” and a cover of “I Love Rock ‘n’ Roll.” The same year as Crossroads, Britney split from boyfriend Justin Timberlake after 3 years of dating. She also appeared in Austin Powers in Goldmember.

In 2003, Britney released her third studio album, In The Zone. The album was a massive hit and included singles “Toxic” and “Everytime.” At the top of 2004, Britney married childhood friend Jason Alexander in Las Vegas. Their marriage was annulled 55 hours later.

Just a few months later, Britney was engaged to dancer Kevin Federline. They married in Oct. 2004. They welcomed their son, Sean Preston, in 2005. Their second son, Jayden James, was born in 2006. In Nov. 2006, Britney filed for divorce from Kevin, and their divorce was finalized in 2007.

Britney’s personal troubles were under constant media and public scrutiny in the late 2000s. Photos of her shaving off all of her hair at an LA salon were made public in Feb. 2007. She lost physical custody of her kids to Kevin in Oct. 2007, but they now have shared custody. She was put on an involuntary psychiatric hold twice in 2008. Amid her personal struggles, Britney’s father, Jamie Spears, enacted a conservatorship over her assets, estate, and business deals. The conservatorship has been in place ever since.

Despite everything, Britney has continued to release new music. She has released 9 studio albums, with her latest album, Glory, being released in 2016. She started her first Las Vegas residency in 2013. She announced a second residency in 2018, but she went on an “indefinite work hiatus” in 2019. She is now dating Sam Asghari.

Over the years, the #FreeBritney movement has gained momentum. The fans involved in the movement want the pop star to be free of legal binding. The recent documentary, Framing Britney, has sparked renewed interest about why Britney still has a conservatorship.

Zoe Saldana

Zoe Saldana
Zoe Saldana then and now. (Everett Collection/AP)

Zoe Saldana, 42, starred as Kit in Crossroads. The same year as Crossroads, Zoe starred in Drumline. Starting in 2009, Zoe began playing Nyota Uhura in the Star Trek film series. She also starred as Neytiri in Avatar and will reprise the role in the upcoming sequels.

The actress began playing Gamora in Guardians of the Galaxy in 2014. She has appeared in several movies within the Marvel Cinematic Universe and is set to return for the third Guardians movie. Zoe is currently filming a new movie from David O. Russell.

Zoe and then-fiance Keith Britton split in 2011 after 11 years. She dated Bradley Cooper from 2011 to 2013. She married Marco Perego in 2013. Their twins were born in 2014. Their third child, a son, was born in 2017.

Taryn Manning

Taryn Manning
Taryn Manning then and now. (Everett Collection/AP)

Taryn Manning, 42, played Mimi in the 2002 movie. She also starred in White Oleander and 8 Mile in 2002. Over the years, she had notable roles in movies like Cold Mountain, Hustle & Flow, A Lot Like Love, and more. One of her most widely-recognized roles was Pennsatucky on Orange Is the New Black. She played the character from 2013 to 2019. She also had an arc on Sons of Anarchy.

Anson Mount

Anson Mount
Anson Mount then and now. (Everett Collection/AP)

Anson Mount, 47, starred as Ben Kimble in Crossroads. He has had a number of television and film roles over the years. He notably played Cullen Bohannon in the AMC series Hell on Wheels, which ran for 5 seasons. He began playing Captain Christopher Pike starting in season 2 of the CBS All Access show Star Trek: Discovery. He is set to star in the Star Trek spinoff, Star Trek: Strange New Worlds.

Justin Long 

Justin Long
Justin Long then and now. (AP)

Justin Long, 42, played Henry in Crossroads. At the time, he was starring in the TV series Ed, which ran until 2004. He’s had other roles in Dodgeball: A True Underdog Story, Accepted, Youth in RevoltVeronica MarsGoing the Distance, and Jay and Silent Bob Reboot. Justin also guest-starred as Paul Genzlinger in 5 episodes of New Girl.

The actor currently hosts his own podcast, Life is Short with Justin Long. He is set to co-write, co-direct, and co-produce the film Lady of the Manor with his brother Christian Long.

Dan Aykroyd

Dan Aykroyd
Dan Aykroyd then and now. (Everett Collection/AP)

Dan Aykroyd, 68, played Pete Wagner, Lucy’s dad, in Crossroads. The SNL alum has starred in several since 2002, including Christmas with the Kranks, 50 First Dates, Tammy, Pixels, and more. He made a cameo appearance in the 2016 all-female reboot of Ghostbusters. Dan will return to his famous Ghostbusters role, Dr. Ray Stantz, in the upcoming 2021 sequel Ghostbusters: Afterlife. In addition to acting, Dan is also a businessman. He co-founded the House of Blues chain and Crystal Head Vodka brand.

Kim Cattrall

Kim Cattrall
Kim Cattrall then and now. (AP)

Kim Cattrall, 64, appeared as Caroline Wagner, Lucy’s estranged mother, in Crossroads. That same year, she won the 2002 Golden Globe for Best Supporting Actress for her performance as Samantha Jones in Sex and the City. The hit HBO series ended in 2004 after 6 seasons. She reprised the iconic role in two Sex and the City movies. However, she will not return for the upcoming Sex and the City revival, And Just Like That.

Kim has starred in several other films since the 2002 release of Crossroads, including Ice Princess, My Boy Jack, and Ghost Writer. She starred in the CBS All Access series Tell Me a Story in 2018 and the FOX series Filthy Rich in 2020.

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