After filming a cameo in the Charlie's Angels movie remake, MTV gross-out comedian Tom Green courts costar Barrymore. The couple begins dating, and she stands by Green during his testicular cancer battle. Green proposes to Barrymore on July 8, 2000 in Cabo San Lucas, Mexico, and she accepts his Tiffany engagement ring. "I was a girl with a crush," Barrymore tells Rolling Stone.
Cameron Diaz, Lucy Liu and Barrymore karate-chop their way through Charlie's Angels, and Barrymore proves powerful behind the scenes as the movie's executive producer. The threesome reunites for the sequel Charlie's Angels: Full Throttle in 2003. Barrymore even convinces movie star Demi Moore to end her nearly six-year hiatus from films and join the sequel's lineup. "We wrote the part for her and wouldn't accept no for an answer," Barrymore tells USA Today of Moore's ex-Angel gone bad role. "We were willing to do whatever it took. Demi was a huge battle for me that I had to win."
After Barrymore and Green escape from their burning Beverly Hills home after their dog Flossie wakes them, the couple gets hitched at a private Malibu estate in front of 100 guests, including Diaz, Liu, Courteney Love, and Adam Sandler. But in December, after five months of marriage, Green files for divorce. "Drew is a wonderful woman," Green, 30, says in a statement. "I love her very much. I wish our marriage could have worked out." The next day, Barrymore issues her own statement: "I love Tom very much. He has always been a great friend and that won't change."
Barrymore, 27, meets Strokes drummer Fabrizio Moretti, 21, at a California concert. The pair quickly hit it off, and by 2004 Barrymore is telling PEOPLE their pairing is "the most positive relationship I've ever been in." The cross-country duo split time between his New York apartment and her L.A. home, skipping many of the high-profile appearances of her past relationships. "We don't walk down the red carpet, and we don't sell out our love," she tells PEOPLE. "That takes a lot of the pressure off us because we don't care what people think."
Baseball fans in Boston go crazy as their long-suffering Red Sox win its first World Series title in 86 years. When the team rushes the field following its Game 4 win in St. Louis, Barrymore and actor Jimmy Fallon are with them, filming the closing scene of their movie Fever Pitch. In the original script, the team wasn't in the playoffs, but the writers make quick adjustments based on real-life occurrences. "When they started winning, I was like, 'What if they…no, don't talk about it! That will jinx it,'" Barrymore tells PEOPLE. "Being at the winning game was a life experience."
After a lifetime of estrangement, Barrymore reunites with her father John as he fights a rare form of bone-marrow cancer. "I don't want to be crippled by things that happened in the past," she tells PEOPLE. "He was a free bird, you know? He couldn't handle being a father." Barrymore visits him during the latter stages of his illness, one time bringing her mother Jaid along to his bedside. "I didn't want to have this closure just for myself," she says. "It was an incredible day."
Months after telling In Style that she's ready to start a family, Barrymore and boyfriend of five years, Fabrizio Moretti, call it quits. But the breakup doesn't break her, as she hosts Saturday Night Live in February for the fifth time and hangs out with newly single gal pal Cameron Diaz. "I think being independent and strong and happy on your own and by yourself, it's probably what will make you a better lover," she tells PEOPLE before reportedly hooking up with Zach Braff and Spike Jonze.
Barrymore graces the cover of PEOPLE's 100 Most Beautiful issue. The 32-year-old actress, who was recently signed as CoverGirl's newest model, considers herself most beautiful "Right after I've worked out and I'm sweating all over the place and my face is two different colors of white and red and my hair is half wet, half dry and I look like I'm about to have a heart attack."
While shooting the romantic comedy He's Just Not that Into You, Barrymore begins dating costar Justin Long, who's also known as the Apple computer commercials' "Mac Guy." After calling Barrymore his "girlfriend" on his official website, Long, 29, takes her home to Fairfield, Conn. for Thanksgiving with his family. The couple seem inseparable, but after nearly a year of dating, Barrymore's rep confirms their split.
The Vogue cover girl gives back in a big way, telling Oprah Winfrey that she is donating $1 million to the World Food Programme to help feed children in Africa. "I have seen with my own eyes what a difference a simple cup of nutritious porridge can make in a child's life," the 33-year-old actress says. "It helps them learn, stay healthy and sets them on track for a bright future."
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