By Bryanne Salazar
8:54am PST, Dec 18, 2017
Have you ever wondered what happened to the most famous celebrities from back in the day? Join Wonderwall.com as we take a look at the biggest names in Hollywood 20 years ago to see what they're up to today… starting with Leonardo DiCaprio. In 1998, the young actor was just 23 and on top of the world after the massive success of "Titanic," which hit theaters in December 1997. While Leo had long been a regular in Tinseltown, the movie launched his career into overdrive, making him one of the most in-demand stars in the biz. Keep reading for more…
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Leonardo DiCaprio, seen here in 2017 with his "Titanic" co-star and close friend Kate Winslet, has had a long and successful run in Hollywood. Along with starring in numerous hit films including "Gangs of New York," "Inception," "Django Unchained" and "The Wolf of Wall Street," in 2004, Leo founded Appian Way Productions, which helped him maneuver his career toward his other love, film producing. Over the years it became apparent to Leo's fans that although his films were amazing and his acting was incredible, he wasn't getting the recognition he deserved (cough, cough, Oscar). That finally changed in 2016 when Leo won a best actor Academy Award for his performance in "The Revenant." Aside from his steady career success, Leo's long been a notorious playboy bachelor, dating some of the most beautiful models in the world like Gisele Bundchen and Bar Refaeli. In 2017, the prominent environmentalist was romantically linked to a handful of young models including German stunner Lorena Rae. Up next for the acclaimed actor and producer are three new films: "Killers of the Flower Moon," "The Black Hand" and "Roosevelt," in which he'll play the title character, Theodore Roosevelt.
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Kate Winslet is possibly even more famous today than she was in 1998. The rising starlet made it her mission to take on diverse and challenging roles following "Titanic," such as Clementine in "Eternal Sunshine of the Spotless Mind," Iris in "The Holiday," Hanna in "The Reader" (which led to her first Oscar for best actress in 2009) and Mildred in the miniseries "Mildred Pierce." In 2017, Kate starred in "The Mountain Between Us" with Idris Elba and the Woody Allen drama "Wonder Wheel." While Kate's career has endured, her love life hasn't been so straightforward. After two failed marriages (that brought forth two amazing children), Kate found her soulmate in businessman Ned Rocknroll, the father of her third child, son Bear Blaze. Up next for Kate is a part in the 2019 TV series "Moominvalley" and a co-starring role in 2020's "Avatar 2."
Will Smith has been really famous for a really long time, but he was at the top of his game in 1998. That's when the "Fresh Prince of Bel-Air" alum, fresh off the fame of his starring role in 1997's "Men in Black," had the world eating out of the palm of his hand. Not only was he a top-billed actor, but he was a top music performer with Grammy-winning hits like "Gettin' Jiggy Wit It" and "Men in Black." Plus, on Dec. 31, 1997, Will married the love of his life, Jada Pinkett Smith — meaning he was also a beaming newlywed (and soon to be second-time dad) in '98.
Like the first two stars on our list, Will Smith managed to stay on a first-name basis with fame. The actor, rapper, husband and father has starred in tons of blockbuster hits like "Ali" and "The Pursuit of Happyness" (both of which earned him Oscar nominations) and family favorites like "Shark Tale" and "Hancock" (as well as two "Men in Black" sequels). In 1999, the actor co-founded the production company Overbrook Entertainment, which produced both of his Academy Award-nominated films as well as "Annie," "I, Robot" and "Secret Life of Bees." In 2017, Will collaborated with DJ Jazzy Jeff on the single "Get Lit," which is Will's first new music project since 2005 (although he did appear on the 2015 remix of "Fiesta"). On a more personal note, Will has remained married for more than 20 years to his beautiful wife Jada Pinkett Smith. Together, they share two (now famous) children, Willow Smith and Jaden Smith. Will is also the father of 25-year-old son Trey Smith from his first marriage to Sheree Zampino. Up next for the prolific actor is the December 2017 crime drama "Bright" followed by two upcoming "Bad Boys" sequels and the highly anticipated 2019 live-action remake of "Aladdin," in which he stars as Genie.
Gwyneth Paltrow became one of the most popular actresses in Hollywood in 1998. That was the year she appeared in a whopping five films, with the last one, "Shakespeare in Love," earning her an Academy Award for her performance. Oh yeah, it didn't hurt that she was also dating one of the hottest guys in the biz, Ben Affleck, after breaking things off with Brad Pitt a year earlier.
Writing a mini bio about Gwyneth Paltrow almost seems unnecessary since she's still a constant presence in the public eye. Over the years, Gwynnie's starred in numerous weird and wonderful films including "Shallow Hal," "The Royal Tenenbaums," all of the "Iron Man" films and even played a recurring character on TV's "Glee" (and won an Emmy for it!). In 2003, Gwyneth and Coldplay frontman Chris Martin tied the knot and later welcomed two kids before announcing their "conscious uncoupling" in 2014. Of course, Gwyneth also famously launched her lifestyle brand, Goop, in 2008. In 2017, Gwyneth reprised her role as Pepper Potts in "Spider Man: Homecoming." She'll return to the role again in 2018 for "Avengers: Infinity War." And if the rumors are true, 2018 could also be the year she walks down the aisle with reported fiance Brad Falchuk.
It's likely you still remember the exact moment you heard Djimon Hounsou speak the powerful words "give us free" in the 1997 historical drama "Amistad." The film launched the little-known West African actor into the realms of superstardom and gave us all someone new and very handsome to crush on.
Djimon Hounsou followed his "Amistad" fame with roles in films like "Gladiator," "Constantine," "In America" and "Blood Diamond" (the latter two earned him Oscar nominations for best supporting actor). For a brief while, Djimon was a regular face on the reality series "Life in the Fab Lane" while he dated the show's star, Kimora Lee. The couple, who broke up in 2012 after spending five years together, share a son, Kenzo (seen here). The actor has branched into TV as well as film, appearing on series like "ER," "Alias," "Black Panther" and "Wayward Pines." In 2017, Djimon had roles in "King Arthur: Legend of the Sword" and "Same Kind of Different as Me" and lent his voice to the animated comedy "Blazing Samurai." In 2018, Djimon will star alongside Matthew McConaughey and Anne Hathaway in "Serenity."
By 1998, everyone in America knew the name Calista Flockhart. That's because she was the star of the very popular TV series "Ally McBeal," which ran from 1997 to 2002 and earned her a Screen Actors Guild Award and Golden Globe. But along with fame came backlash as fans and critics accused the petite actress of having an eating disorder. The rumors intensified after Calista appeared at the Emmy Awards looking noticeably thinner. Later, the actress gave a candid interview to People magazine in which she claimed, "I guess I don't know the exact definition of anorexia," which many took as an admission by omission. Still, Calista's fame continued to rise.
Calista Flockhart overcame intense media scrutiny of her body and managed to parlay her success into a lasting career. After a brief stint on the big screen in the films "The Last Shot" and "Fragile," Calista returned to television with a recurring role on the series "Brothers & Sisters" that ran from 2006 to 2011. Calista took on minor roles for a few years after the show ended but in 2015 was cast as Cat Grant in the action series "Supergirl." On a more personal note, Calista opened up in 2006 with reporters and shared that she did have an unhealthy relationship with food early in her career, claiming she "under-ate and over-exercised" to stay thin. Thankfully, she's in a healthier place now. In 2010, she wed actor Harrison Ford, who she'd been dating since 2002. Together, they're raising her adopted son, Liam, who's seen here with Harrison and Calista in 2017. No word yet on what's to come for Calista in 2018.
While Ben Affleck had been working steadily in Hollywood since 1986, his big break came in 1997 with the release of the film "Good Will Hunting," which he both starred in and wrote (along with best friend Matt Damon). The film earned Ben and Matt the Academy Award for best original screenplay in 1998 and launched both of their careers into overdrive. To add to Ben's appeal, he'd also won the heart of Hollywood's newest darling, Gwyneth Paltrow.
Ben Affleck's Hollywood tale over the last 20 years isn't as straight and narrow as it was for many of the stars on our list. While he enjoyed success in numerous films including "Armageddon, "Pearl Harbor," "Hollywoodland" and "Argo" — which he also directed (it won a best picture Oscar too) — he had a series of personal troubles and doomed relationships that kept him in the tabloids. After parting ways with Gwyneth Paltrow in 2000, Ben embarked on one of his most high-profile relationships ever — with singer and actress Jennifer Lopez, which led to the nickname "Bennifer" and a quick engagement. That relationship ended a few years later and things seemed to cool down when Ben and actress Jennifer Garner linked up, leading to 10 years of marriage and three children. Sadly, that relationship ended with a divorce filing. Throughout the years, Ben's been open about his struggles with alcoholism and sobriety. In 2017, he revealed he'd again completed rehab, went public with "Saturday Night Live" producer Lindsay Shookus and starred in "Justice League" as Batman — a role that he may or may not reprise in the upcoming action adventure film "The Batman" and "Justice League Part Two."
Helen Hunt could do no wrong in 1998. The "Mad About You" star won three major awards for best actress that year — a SAG Award, a Golden Globe and an Oscar — for her performance in the 1997 romantic dramedy "As Good As it Gets" co-starring Jack Nicholson. Her sudden accolades meant the future was very bright for Helen.
Helen Hunt signed off from "Mad About You" in 1999, the same year she wed longtime love Hank Azaria, to embark on a new film career. The actress landed roles in major motion pictures like "Pay it Forward," "Castaway" and "The Sessions," which earned Helen her second Oscar nomination, but largely stayed out of the spotlight. In 2000, after just a year of marriage, Helen and Hank divorced, almost as quietly as they married. A year later, Helen began dating producer, writer and director Matthew Carnahan. The couple welcomed a daughter, Makena, in 2004. Sadly, in 2017, Helen and Matthew split over alleged "trust issues." The actress, who co-starred in the crime drama "Shots Fired" in 2017, will next appear in the 2018 big-screen drama "The Miracle Season."
LL Cool J had been a force in the rap world since the late '80s but in 1998, he was earning praise as a talented actor as well. That year, LL, who'd just released third single "Father" off his "Phenomenon" album (which landed on Billboard's Top 100 songs of the year list), took on roles in films like "Halloween H20: 20 Years Later," "Caught Up" and "Woo" while also starring on the hit series "In the House" and appearing on an episode of one of the biggest TV dramas in the nation, "Oz." Plus, his music from 1997 (like "4, 3, 2, 1" and "Candy") was still heating up the airwaves.
Today, LL Cool J fans likely first think of him as an actor, but he's continued making music over the last 20 years. In fact, LL's released six additional albums and has another in the works. His 2000 album, "G.O.A.T.," reached No. 1 on the Billboard 200 and has been his most successful musical release to date. Along with hit songs, LL has continued to rise as a prominent actor in Hollywood. He's appeared in numerous films including "Charlie's Angels," "Any Given Sunday" and "Last Holiday" and has appeared on multiple TV shows like "30 Rock," "House" and "Hawaii Five-0." In 2009, he started his long run on the hit television drama "NCIS: Los Angeles," on which he continues to star to this day. And from 2012 to 2016, he drew raves as the host of the annual Grammy Awards. In 2015, he became the executive producer and co-host of the wildly successful competition series "Lip Sync Battle," which was renewed for a fourth season in 2018. He's been married to Simone Smith since 1995. They have four children.
Although Canadian songbird Sarah McLachlan had been a part of the music scene since 1988, it wasn't until mid-1997 that she resurfaced on the airwaves and caught the attention of a whole new generation of fans with her album "Surfacing." Well into 1998, the album (which peaked at No. 2 in the U.S.) was producing hit singles like "Adia" and "Building a Mystery" that were constantly on the radio. Also in 1998, Sarah's song "Angel" was included on the soundtrack to the hit movie "City of Angels" starring Meg Ryan and Nicolas Cage. That same year, Sarah won two Grammy Awards and her single "Adia" was included in Billboard's Top 100 songs of the year list.
Sarah McLachlan has spent the last 20 years making the world swoon with her rich, sultry voice and enchanting lyrics. After the success of her album "Surfacing," Sarah released her first live album, "Mirrorball," in 1999, which included a live version of her 1995 hit song "I Will Remember You." The song found renewed popularity and went on to win Sarah her third Grammy. Seven albums followed, including five new music compilations and two more live albums. Sarah was also responsible for the wildly popular all-female musical tour "Lilith Fair," which debuted in 1997 and returned in 1999 and 2010. Known for her passion for animal rights, Sarah has lent her music (in particular, the song "Angel") to the ASPCA for use in its heartbreaking advertisements. Her most recent album, "Wonderland," dropped in 2016 and was nominated for a Grammy. She's kept a low profile in 2017 but if history is any indicator of what's to come, we're likely to hear new music from Sarah in the near future. Sarah, who divorced drummer Ashwood Sood in 2008 after 11 years of marriage, is raising their two teen daughters, India and Taja.
Matt Damon was a young actor in Hollywood for nine years before he became a household name with the 1997 release of the film he both co-wrote and starred in, "Good Will Hunting." The movie's phenomenal success won him and writing partner/BFF Ben Affleck an Oscar for best screenplay in 1998 and opened the door for new movie roles and screenplay work. That same year, Matt starred in two big-budget films, "Saving Private Ryan" and "Rounders," proving he was far more than a one-hit wonder.
As just about everyone in the world already knows, Matt Damon spent the last 20 years endearing himself to us on the big screen, both on-camera and behind the scenes. Over the years, Matt's starred in blockbuster hits like "Oceans 11" and "The Bourne Identity" and their sequels as well as dramas like "The Departed" and "The Martian" (which earned him his second Golden Globe Award). In 2012, he along with buddy Ben Affleck opened the production company Pearl Street Films, which is behind movies like Oscar winner "Manchester by the Sea." From 2001 to 2015, Matt executive produced the TV series "Project Greenlight" and has worked as a producer on numerous documentaries including "Running the Sahara," "People Speak" and "Bending the Arc." In 2005, Matt married Luciana Barroso. They have four daughters.
Lauryn Hill had an incomparable sound and in 1998, she branched off from The Fugees to debut her solo album, "The Miseducation of Lauryn Hill," which reached No. 1 on the Billboard 200 and R&B charts. It launched hit singles "Doo Wop (That Thing)" and "Everything is Everything," which both received major attention on the airwaves (leading some critics to consider Lauryn the next big thing in the world of music). It didn't hurt that she also took home an astonishing four Grammy Awards that year.
Sadly, a life of fame wasn't in the cards for Lauryn Hill. The reclusive singer never followed up with another studio album, leaving fans confused. Lauryn has claimed she moved "underground" to separate herself from the "media-protected military industrial complex" while surrounding herself with "like-minded people." She did release a live album via MTV Unplugged in 2002, which peaked at No. 3 on the Billboard 200, but after that, little was heard from her. That is until 2012, when Lauryn was brought up on tax evasion charges, to which she plead guilty. In 2013, the singer and mother of six served a three-month prison term for the crime. After getting out, she started touring and performing at festivals, though repeatedly made headlines for taking the stage hours late. In 2015, she recorded six songs for a Nina Simone documentary soundtrack album. Lauryn was previously in a committed relationship for 13 years with Bob Marley's son, Rohan Marley, who fathered five of her six children. The couple separated in 2009. In 2017, Lauryn became a first-time grandmother when son Zion — the child she sang about on her brilliant 1998 solo album — welcomed his first child.
