Biggest stars of 1999 - Where are they now? | Gallery

By Megan Riedlinger 9:06am PST, Dec 26, 2018

It's hard to believe that 1999 was two decades ago! In honor of the epic year filled with boy bands, pop princesses and amazing teen movies, Wonderwall.com is checking up on some of the biggest stars of '99. First up is Jason Biggs, the lead actor in one of the most talked-about comedy flicks of the year, "American Pie." So what's he doing now? Keep reading to find out!

After "American Pie," Jason Biggs starred in 2000's"Loser," another teen rom-com, with fellow '90s star Mena Suvari. That was followed up by even more comedies, including 2001's "Saving Silverman" and the "American Pie" sequels "American Pie 2″and "American Wedding." He filled the rest of the '00s with less notable flicks like "Eight Below" and "My Best Friend's Girl" before starring in another "American Pie" installment, "American Reunion," which hit theaters in 2012. Jason transitioned to the small screen with a role on Netflix's "Orange Is the New Black" beginning in 2013, and has since appeared in a handful of TV movies and one-off episodes on TV. These days, the best place to find Jason is social media. He's outspoken on Twitter — which has sparked his fair share of controversy. In 2012, he wrote offensive jokes about presidential nominee Mitt Romney's wife, Ann, and vice presidential nominee Paul Ryan's wife, Janna, and he's since made some distasteful jokes about tragedies like the doomed Malaysia Airlines flight and the death of "The Bachelorette" contestant Eric Hill in 2014. Jason has been married to Jenny Mollen, a co-star in his 2008 flick "My Best Friend's Girl," since 2008. They share two sons, Sid, born in 2014, and Lazlo, born in 2017.

Rachael Leigh Cook's breakout role came in 1999 in the teen romantic-comedy "She's All That" opposite Freddie Prinze Jr., which went on to become one of the biggest teen movies of the '90s. So where did Rachael end up?

Rachael Leigh Cook has continued to work steadily but never truly duplicated the success of "She's All That." Though the 2001 flick "Josie and the Pussycats" was primed to be her next big hit, it ended up flopping at the box office. She starred alongside Emma Roberts in the teen detective flick "Nancy Drew" in 2007 and has since appeared in numerous made-for-TV movies. She also had notable roles on TV's "Psych" from 2008 to 2010 and "Perception" from 2012 to 2015. More recently, Rachael's been appearing in Hallmark Channel films like "Autumn in the Vineyard," "Summer in the Vineyard" and the 2018 holiday flick "Frozen in Love." As for her personal life, Rachael has been married to actor Daniel Gillies since 2004. They share two kids: daughter Charlotte (born in 2013) and son Theodore (born in 2015).

1999 was the year of Britney Spears! Her debut album, "…Baby One More Time," was released that January, turning her into a bona fide pop star. What's Britney up to these days?

In the last two decades, Britney has released eight more albums — from "Oops!… I Did It Again" in 2000 to "Circus" in 2008 to her most recent, "Glory" in 2016. She's also dotted her illustrious career with some acting gigs like a starring role in the 2002 film "Crossroads" and has bagged lucrative endorsement deals with brands like Pepsi and "Candie's." She's also launched successful perfumes and video games and has even written books including two with mom Lynne Spears, "Heart to Heart" and "A Mother's Gift." On the personal front, Britney has been the subject of much tabloid fodder. From her quickie Vegas wedding to childhood pal Jason Alexander and her failed marriage to backup dancer Kevin Federline (with whom she shares sons Sean Preston, born in 2005, and Jayden James, born in 2006) to her now infamous 2007 mental breakdown, Britney's every move has been scrutinized since she found fame. These days, though she remains under a conservatorship led by her father, Jamie, Britney's life is great: Following a string of failed romances, she's been with fitness model Sam Asghari since 2016 and is returning to Las Vegas for a new residency, "Britney: Domination," which is set to begin in February 2019.

Back in 1999, David Boreanaz nabbed his own "Buffy the Vampire Slayer" spin-off in the form of The WB's "Angel." The show, which followed his vampire character's story as he moved to Los Angeles, became an instant hit thanks to die-hard "Buffy" fans. What is David doing today?

David Boreanaz continued to find success on the small screen after "Angel" ended in 2004. In 2005, he began starring on the FOX series "Bones" (alongside Emily Deschanel), a wildly successful drama that ran for 12 seasons until its end in 2017. Once that show was over, David jumped to the CBS series "SEAL Team" in 2017. The successful TV actor is currently married to second wife Jaime Bergman, with whom he shares son Jaden (born in 2002) and daughter Bella (born in 2009). He made tabloid headlines in 2010 when it was revealed he'd cheated on his then-pregnant wife with Rachel Uchitel (of Tiger Woods affair fame), though David and Jaime worked through his infidelity to keep their marriage intact.

Jennifer Love Hewitt was a real It girl back in 1999 thanks to her success on FOX's "Party of Five" and appearances in huge '90s flicks like "I Know What You Did Last Summer" and "Can't Hardly Wait." 1999 marked the end of "Party of Five," the beginning of her short-lived spin-off "Time of Your Life," and the release of her hit single "How Do I Deal."

Jennifer Love Hewitt's popularity continued to soar in the early '00s as she starred in flicks like 2001's "Heartbreakers" alongside Sigourney Weaver and 2002's "The Tuxedo" with Jackie Chan. 2005 saw her returning to television with "Ghost Whisperer," which ran for five seasons before its cancellation in 2010. In 2012, she landed her next show, "The Client List," which ran until 2013, at which point she switched gears and joined the cast of "Criminal Minds" from 2014 until 2015. These days, you can see Jennifer on FOX's hit show "9-1-1." Offscreen, Jennifer has been married to her "The Client List" co-star Brian Hallisay since 2013. They share daughter Autumn (born in 2013) and son Atticus (born in 2015).

The world fell in love with the little boy who starred opposite Adam Sandler in 1999's "Big Daddy." In real life, the character of Julian McGrath was played by twins — Dylan Sprouse and Cole Sprouse. So where are the boys today? (You might already know the answer to this one!)

"Big Daddy" was the Sprouse twins' first major role. Cole Sprouse and Dylan Sprouse continued to act through the '00s, eventually landing a big hit show, the Disney Channel series "The Suite Life of Zack & Cody." That ran from 2005 until 2008 and was followed by the spin-off "The Suite Life On Deck" plus appearances on other Disney shows like "Wizards of Waverly Place," "Hannah Montana" and "So Random!" These days, the brothers have gone their separate ways professionally. Cole stars on the hugely popular CW drama "Riverdale," where he met current girlfriend Lili Reinhart. Dylan has lended his voice to video games like "Dungeons & Dragons" and focused on indie acting projects. More recently, he played the love interest in Camila Cabello's music video for "Consequences," though offscreen, he's happily dating model Barbara Palvin.

1999 brought the found-footage phenomenon to the big screen in "The Blair Witch Project," an indie film that terrified audiences everywhere as many viewers believed the documentary-style movie was showing real-life events. The fact that marketing campaigns listed the actors as "missing" or "deceased" brought another level of speculation and horror over whether or not the film's events actually happened. It turned out it was all fake and main character Heather Donahue was not really a student filmmaker but an actress. So where is she today?

Heather Donahue's performance in the polarizing "The Blair Witch Project" led to a Razzie Award for worst actress. She followed up the hugely successful flick with a film co-starring big '99 stars Freddie Prinze Jr. and Jason Biggs, "Boys and Girls." But other than that, Heather largely stayed in the independent film world. She moved to the small screen, appearing on episodes of "Without a Trace" and "It's Always Sunny in Philadelphia" before retiring from acting completely in 2008. So what did Heather do next? The former actress got into the world of growing medical marijuana and even wrote a book about her new career path, "Growgirl: How My Life After The Blair Witch Project Went to Pot," which was released in 2012.

October 1999 saw the debut of an addictive new The WB show about some gorgeous and mysterious aliens. "Roswell" was an instant hit, catapulting star Shiri Appleby to fame. See Shiri now…

Shiri Appleby went on to star on a few other television shows in the '00s like ABC's "Six Degrees" and NBC's "ER." 2010 saw her on the WB's successor, The CW, on the show "Life Unexpected," but it wouldn't be until 2015 that she had another huge hit on her hands. Shiri played the lead on Lifetime's cult hit "UnREAL," which wrapped its fourth and final season after moving to Hulu. Shiri is married to restauranteur Jon Shook (the co-owner of Los Angeles hotspots Animal, Son of a Gun, Trois Mec and Jon & Vinny's), with whom she shares daughter Natalie, born in 2013, and son Owen, born in 2015.

Ricky Martin had a massive hit with 1999's "Livin' La Vida Loca," which ushered in a Latin music explosion as he transitioned his Spanish-language career to the English market. We'll check in with Ricky 20 years later next…

Ricky Martin's self-titled English-language debut album helped launch his career in the States, and he followed it up with two more English-language albums and three more Spanish-language albums in the years that followed. Aside from continuing to work on his music, he's also flexed his acting muscles. He returned to Broadway in 2012 (having previously starred in Les Miserables in 1996) to appear in "Evita." He also did some work on television, appearing on "Glee" in 2012 and then re-teaming with creator Ryan Murphy to step into the role of Antonio D'Amico, Gianni Versace's lover, in the 2018 project "The Assassination of Gianni Versace: American Crime Story." As for his personal life? Ricky was in a relationship with Mexican TV host Rebecca de Alba for 14 years before coming out as a gay man in 2010. He welcomed twin boys, Matteo and Valentino, via surrogate in 2008 and in early 2018, Ricky announced that he'd quietly married artist Jwan Yosef after a few years of dating.

The Ryan Murphy-helmed "Popular" debuted on The WB in 1999 and made a splash on the teen-geared network. Star Leslie Bibb made a name for herself that year after landing the role of popular girl Brooke McQueen. She also starred in the 1999 big-screen thriller "The Skulls" alongside late-'90s megastars Joshua Jackson and the late Paul Walker. What's Leslie up to these days?

After 1999, Leslie Bibb bounced between TV and film. Her most notable roles have included a recurring part on NBC's "ER," a memorable turn as Will Ferrell's character's wife in 2006's "Talladega Nights: The Ballad of Ricky Bobby," and a great part as the rival of Isla Fisher's character in 2009's "Confessions of a Shopaholic." Leslie also starred in 2008's "Iron Man" and its 2010 sequel, which are her biggest box-office successes to date. More recently, she played a hilarious recurring character on the ABC sitcom "American Housewife." As for her personal life, she's been dating actor Sam Rockwell since 2007. They've shared the screen in "Frost/Nixon," "Iron Man 2" and "Don Verdean."