Drew Barrymore  turns 40 this week, but there was a time when she was just a young 20-something making her way in Hollywood. How did her 20s compare to other famous women who spent their coming-of-age years in the spotlight? We're taking a look back on what Beyoncé Knowles, Angelina Jolie , Gwyneth Paltrow , and more starlets were up to at age 20. What did their careers look like? Who were they dating? Digging into their pasts to gain some perspective, we're sharing a glimpse of how these successful women spent their 20th year. As part of the starlet time machine, we also hunted down a quote from each celebrity at that age, shedding even more light on who they were at the time. Go back in time with a look at these 20 famous faces at age 20, and then see what the guys were up to at the same age .
Current age: 33
Career at 20: Britney Spears  celebrated her 20th birthday in December 2001, just after the release of the Britney album and the start of her Dream Within a Dream tour. In 2002, her movie Crossroads was released, and she was back in the studio recording her next album, In the Zone, at the end of the year.
Relationship status at 20: Britney and then-*NSYNC member Justin Timberlake  broke up in 2002 after dating for nearly three years, and he went on to release "Cry Me a River" in November of that year, which is rumored to be about Britney cheating on him.
Quoted at 20: In October 2002, Britney opened up about fame  in Rolling Stone, saying, "I feel changed. I'm a little more serious than I was. It's really weird, because you're a star, and everything is about you all the time — and I'm tired of that. I want to have a different perspective. And not have all my family and all the people I know working for me. I want to hang out with my friends and be a nobody. Because that's how you become reinspired."
Current age: 39
Career at 20: Angelina's first major film, Hackers, debuted in 1995.
Relationship at 20: On the set of Hackers, Angelina began a romance with her British costar, Jonny Lee Miller. They married on March 28, 1996, when Angelina was 20 and Johnny was 23. The bride wore rubber pants and a white t-shirt that had the groom's name written in her blood.
Quotes at 20: Angelina didn't try to hide her drug experimentation, like many starlets do today. In an interview, she said : "I have done just about every drug possible: cocaine, ecstasy, LSD and, my favorite, heroin."
Current age: 35
Career at 20: In 1999, Claire was studying at her dad's alma mater, Yale University, before eventually dropping out the following year. With Romeo & Juliet and her Emmy-nominated days on My So-Called Life behind her, she appeared on the big screen multiple times in 1999 with roles in The Mod Squad and Brokedown Palace.
Relationship status at 20: She was linked to Australian singer Benjamin Lee, whom she dated from 1997 to 2003.
Quoted at 20: During an appearance on David Letterman , Claire opened up about her break from acting, saying, "I've just been going to school, and, you know. I just finished my first year at Yale, which was a huge relief. It's really rigorous, but there's some fun to be had."
Current age: 34
Career at 20: Coming off being named model of the year at the VH1/Vogue Fashion Awards in 1999, Gisele began her reign as a Victoria's Secret Angel in 2000. That year she secured a $25 million, record-breaking contract with the lingerie brand, and Rolling Stone put Gisele on its cover, calling her the most beautiful girl in the world.
Relationship at 20: In 2000, Gisele started her five-year relationship with Leonardo DiCaprio .
Quoted at 20: In an interview with Time magazine, Gisele humbly explained her appeal: "I think guys like me because they like girls in lingerie. They like any girl in lingerie."
Current age: 42
Career at 20: In September 1992, Gwyneth Paltrow  was right at the start of her career, following a small role as young Wendy in 1991's Hook and a quick cameo in May 1992's Cruel Doubt, which starred her mother, Blythe Danner. She also starred in the made-for-TV movie Deadly Relations.
Relationship status at 20: Her first publicized romance didn't come until age 24, when she was engaged to Brad Pitt , whom she dated from 1994 to 1997.
Quoted: Gywneth's career hadn't taken off yet when she was 20, but at 21, she sat down for an interview and talked about what she hoped for herself , saying, "I think I would like to do the roles that are interesting. I would like to do everything — comedy and drama — as long as the characters have real substance to them. I'm not interested in being, you know, that sort of set-decoration woman at all."
Current age: 28
Career at 20: Just My Luck and A Prairie Home Companion, which costarred Meryl Streep , were released in the months before Lindsay's 20th birthday, and next came Bobby in November 2006 and Georgia Rule in May 2007.
Relationship status at 20: Lindsay went through a few personal struggles in 2006 and 2007, including a DUI arrest and a rehab stint. During that time, she and Hard Rock Cafe heir Harry Morton broke up , and in May 2007, she was linked to Calum Best , a British TV personality.
Quoted at 20: For Lindsay's August 2006 Elle interview , the actress talked about all her tabloid coverage. "You kind of ask for it when you go to nightclubs," she said. "People are like, 'Just don't go out!' but I can't help it. I literally come out of my hotel and the [photographers] are there. It's not like I ask them to follow me. But you know, it's actually weird when the paparazzi's not there and things aren't being written, because you kind of wonder, 'Do people not care anymore?'"
Current age: 41
Career at 20: Kate kicked off the waify, "heroin-chic" look of the early 1990s after she became the face of Calvin Klein  in 1994. She starred in the now-infamous ads for Obsession, CK One, and Calvin Klein Underwear  alongside Mark Wahlberg . That same year, she also made her first appearance in the Pirelli calendar and on the cover of British Vogue.
Relationship status at 20: Kate dated Johnny Depp  for four years from the time she was 20. They were engaged for a couple of months before calling it quits in 1998.
Quoted: While she's often mum, Kate did talk about being 20 in her book: "At the age of 20, I have traveled all over the world and have seen and learned about many different cultures, an education that is not available in any school. I consider myself extremely lucky. I also realize that with any amount of good, comes a certain amount of bad. That's fine. A lot of horrible, unfair, untrue things have been said about me. I've been labeled viciously by the majority of the media, which in turn has fueled the rumor mill. I can only say that the best revenge is success, and that the more visible they make me, the more invisible I become."
Current age: 32
Career at 20: In February 2002, about six months after the release of The Princess Diaries, Anne Hathaway  took to the NYC stage to play Lili in a production of Carnival! Later that year, she starred opposite soon-to-be Christian Grey actor Charlie Hunnam  in Nicholas Nickleby.
Relationship status at 20: Anne didn't publicly date anyone at that time, but rumors linked her to Hugh Dancy, now married to Claire Danes .
Quoted at 20: A few months before turning 20, Anne was interviewed by the BBC , and she was asked about being typecast after her role in The Princess Diaries. "Well, actually, in my next movie, I am playing a drug-addled prostitute," she joked. "Just kidding. I'm going to school right now, so it'll have to be something pretty special to pull me out of that. If I find it, wonderful, if not, I'm going to graduate with my degree in English and I'll take it from there." Anne eventually finished her degree at NYU.
Current age: 33
Career at 20: In October 2001, just after Beyoncé's Sept. 4 birthday, Destiny's Child released their holiday album, 8 Days of Christmas. Shortly after the album's release, the group announced that they were going on a hiatus to pursue solo careers, and the following Summer, Beyoncé appeared as Foxxy Cleopatra in Austin Powers in Goldmember.
Relationship status at 20: It's rumored that Beyoncé started dating Jay Z around 2001, but the two were first publicly linked when she collaborated on his October 2002 single "'03 Bonnie & Clyde ," which they performed together on TRL the following month.
Quoted at 20: While promoting Austin Powers in Goldmember in 2002, Beyoncé was interviewed in the UK  and talked going solo. "When you start a new chapter in your life, everything is just scary. It's a good scariness, because it forces you to grow. My main thing is performing by myself, like I can't imagine that. That's why in our show a year ago we started doing one song by ourselves, just so we could get comfortable with that, because we knew after the tour that we'd start individual projects . . . The first couple times, I forgot the words!"
Current age: 39
Career at 20: Drew turned 20 in February 1995, just a month after she appeared nude for Playboy. For her birthday, Steven Spielberg , who directed her as child in E.T., gave her a quilt and a note that said, "Cover yourself up." That year, she starred in Boys on the Side with Whoopi Goldberg and Mad Love opposite Chris O'Donnell. She also made a cameo in Batman Forever.
Relationship status at 20: Drew was linked to Hole's lead guitarist Eric Erlandson in 1995, whom she likely met through Courtney Love — Drew is the godmother of Frances Bean Cobain , the daughter of Courtney and the late Kurt Cobain.
Quoted at 20: Drew Barrymore 's 1995 late-night appearance with David Letterman  made headlines, mostly because at one point, she hopped up on his desk to dance for David and ended up flashing him before kissing him on the cheek. During the interview, she also shared details about her recent 20th birthday, saying, "It was my first birthday of my whole life that I enjoyed, because normally on my birthday I pretty much sit in the bathtub and cry . . . I have no problem with age, it's just the celebratory day — a day all about you — it makes you kind of nauseous."
Current age: 26
Career at 20: Days after her 20th birthday in Feburary 2008, Rihanna  attended the Grammys, where she presented and won the award for best rap/sung collaboration with Jay Z for "Umbrella." That year, she also joined Kanye West , Lupe Fiasco, N.E.R.D., and Nas for the Glow in the Dark Tour. She also released several successful singles, including "Disturbia" and "Take a Bow."
Relationship status at 20: Rihanna  was in a relationship with Chris Brown  when she turned 20 in 2008, and he joined her for several stops on the Glow in the Dark Tour. The two broke up just after her 21st birthday in February 2009 as reports surfaced of assault.
Quoted at 20: Rihanna sat down with Cosmopolitan in 2008 , where she talked about her success and how it helped her confidence. "A year ago, I would have sat here in my shell with my hands in my lap and been very shy. But now, I can be goofy and outgoing." Later, she said, "Some people never figure themselves out, and that's sad. I'm still learning who I am, but I'm not scared to be myself anymore."
Current age: 32
Career at 20: After turning 20 in July 2002, Anna promoted the film 25th Hour, which was released in December of that year. The star-studded movie featured Edward Norton , Philip Seymour Hoffman , Rosario Dawson , and Anna, among others. That Spring, in May 2003, X2 hit theaters, and she and costar Shawn Ashmore were nominated for two awards: the MTV Movie Award's best kiss award and the Teen Choice Award for best onscreen chemistry.
Relationship status at 20: Anna didn't have any public relationships in her early 20s, but rumors linked her to Joaquin Phoenix , who played her dad in Buffalo Soldiers.
Quoted at 20: During an appearance on The Daily Show With Jon Stewart  in December 2002, Anna talked about going to school at Columbia University, saying, "Being around people my age is kinda nice — not being the youngest person by 15, 16, 20 years, you know?"
Current age: 24
Career at 20: In 2010, Emma ended her freshman year at Brown University, then kicked off her second before taking a break and eventually returning in Fall 2013. She also wrapped up filming for the Harry Potter franchise in 2010, promoting the first installment of the final chapter. Afterward, no longer having to play Hermione Granger, she cut her hair into a pixie cut. Emma also began negotiations for her role in The Perks of Being a Wallflower and starred in the "Say You Don't Want It" music video  for the British indie band One Night Only.
Relationship status at 20: Emma has been quiet about her personal life over the years, but she did say that fame made dating difficult  at Brown, explaining that people must have been intimidated by the "fame wall."
Quoted at 20: In the December 2010 issue of Marie Claire , Emma talked about growing up, saying, "To be honest, I've always had far too much freedom. I had a job when I was 10. I started living on my own when I was 17 or 18. I've earned my own money; I've traveled the world. What would I rebel against?"
Current age: 34
Career at 20: Michelle Williams  turned 20 in 2000, just before her fourth of six seasons on Dawson's Creek.
Relationship status at 20: Michelle Williams has stayed mostly quiet about her personal life over the years, but she was linked to Bright Eyes singer Conor Oberst around 2000.
Quoted: In 2010, Michelle discussed her Dawson's Creek years , saying, "I said to a friend [that] being on Dawson's Creek was kind of like being a mobster. You set up a shop selling pizza but in the back you're laundering money. You're doing one thing in plain sight and secretly plotting something else. I was plotting my tastes, my interests, my beliefs and hopes for what I could be . . . Yes, it was hard getting jobs I wanted. I was a pop tart. It took patience and baby steps. I did a play in New York that wasn't about being blonde, which led to a role in an HBO thing to a role in a British drama. As F. Scott Fitzgerald said, 'Gradually, then suddenly.'"
Current age: 24
Career at 20: Jennifer Lawrence  had her breakout role with 2010's Winter Bone, which premiered at the Sundance Film Festival that year. Praise poured in from critics, and she received an Oscar nomination for best actress for her performance.
Relationship status at 20: She met her current boyfriend, Nicholas Hoult, on the set of X-Men: First Class that year.
Quoted at 20: During promotions for Winter's Bone, Jennifer sat down with Tribute Movies and talked about preparing for fame , saying, "I don't know if it's something you can prepare for — I'm just always going to focus on the work. And I have my mom who constantly tells me I'm not talented. I'm kidding, she doesn't."
Current age: 25
Career at 20: Taylor Swift  turned 20 at the end of 2009, the year she was interrupted by Kanye and named artist of the year by Billboard. In January 2010, she won four Grammys, including album of the year for Fearless. The buzzed-about album also garnered her top awards at the American Music Awards and the Country Music Awards, and she was part of Time's 2010 list of 100 most influential people. Meanwhile, on top of her Fearless tour, Taylor also made her big-screen debut in 2010 with Valentine's Day.
Relationship status at 20: Taylor's relationship with Taylor Lautner  ended right around her 20th birthday in December 2009, and she was soon linked to John Mayer . Toward the end of 2010, she dated Jake Gyllenhaal .
Quoted at 20: In October 2010, Taylor opened up to Glamour  about her whirlwind year. "I've gone through a few different phases of gratitude," she said. "When it's happening, you're all about [what's next] and trying not to make a misstep. When it came time to lock myself away and make my next album, I had a feeling of, 'Wow, that really was something, wasn't it?' I drive down the same streets I used to drive years ago, when I was just dreaming about stuff like this. So I feel total happiness and anticipation for the next thing."
Current age: 32
Career at 20: Just after Kirsten's 20th birthday in April 2002, she was busy promoting her blockbuster film Spider-Man, which hit theaters that May. She also started filming 2003's Mona Lisa Smile that Fall, working alongside Julia Roberts , Maggie Gyllenhaal , and Julia Stiles.
Relationship status at 20: After being linked to her Spider-Man costar Tobey Maguire  in 2001, Kirsten dated Jake Gyllenhaal , whom she met through her Mona Lisa Smile costar Maggie Gyllenhaal. The pair dated from September 2002 to July 2004, at one point moving in together and sharing a dog .
Quoted at 20: In 2002, Kirsten was interviewed about Spider-Man  and discussed the famous upside-down kiss scene: "We had that huge rain scene, which was so cold. That was pretty challenging, to act all romantic and like you were warm in the Summer rain or whatever time of year it was supposed to be. But really it was so cold."
Current age: 24
Career at 20: 2010 was an especially busy year for Kristen Stewart . In March, a few weeks before Kristen's 20th birthday, The Runaways was released. That June, the third Twilight movie, The Twilight Saga: Eclipse, also hit theaters. She even took the top spot on Vanity Fair's list of highest earning female actresses of 2010.
Relationship status at 20: Although the pair hadn't yet confirmed their relationship, Kristen was linked to her Twilight costar Robert Pattinson .
Quoted at 20: In the May 2010 issue of Elle , Kristen talked about the wild side of fame. "Once somebody finds out, you have to get the hell out of wherever you are. People freak out. And the photographers, they're vicious. They're mean. They're like thugs. I don't even want to drive around by myself anymore. It's f**king dangerous."
Current age: 27
Career at 20: Hilary turned 20 six months after the release of Dignity, her fourth album, which featured a worldwide tour by the same name and the single "With Love." She also played a pop star in the May 2008 movie War, Inc. alongside John Cusack .
Relationship status at 20: Hilary was first linked to her now-husband, former NHL player Mike Comrie, in Summer 2007.
Quoted at 20: Hilary told Cosmopolitan in January 2008  that she was starting to feel more like an adult, saying, "This has been a big cleansing year for me. I learned a ton about myself, and I became really independent. I feel like I grew up a lot."
Current age: 33
Career at 20: Nicole studied arts and media at the University of Arizona for two years before dropping out and returning to LA. She admitted to experimenting with drugs at this age and eventually did a stint at the Sierra Tucson drug rehab center after being caught with heroin. Fame wouldn't come until 22, when Nicole starred alongside her then-BFF Paris Hilton  in the reality show The Simple Life.
Relationship status at 20: Nicole was linked to Cher's son Elijah Blue Allman before she began dating Adam Goldstein (otherwise known as DJ AM) in 2003.
Quoted: While Nicole didn't pop up on the public's radar until 2003, she recently reflected on her 20s in an interview with Ocean Drive magazine , saying, "The mistakes my parents made in their 20s weren't documented, and the mistakes that I made in my 20s were. I don't know anybody who can look back at who they were at 20 and say, 'I'm the exact same person.' It's all about evolving and growing."