After starring in the ensemble romantic comedy He's Just Not That Into You, Barrymore switches gears to portray Edith "Little Edie" Bouvier Beale, Jacqueline Kennedy Onassis' reclusive first cousin, in the HBO movie Grey Gardens. The film attracts 2.7 million viewers by weekend's end, making it HBO's most watched TV movie since 2004.
At the premiere of her HBO flick Grey Gardens, Barrymore cozies up to former flame Justin Long. "I adore him," she says. "And I thank God that my friend supports me the way he does." While neither confirm being back on, they reunite onscreen in the hit romantic comedy Going the Distance.
Barrymore takes her first shot at directing for Whip It, a coming-of-age comedy starring Juno's Ellen Page who joins an all-girl roller derby team. "I like movies about girls who are capable," she says.
Barrymore wins her first Golden Globe for lead actress in a TV movie for HBO's Grey Gardens – which is also named best TV movie. "I've been in the room since I was 7 years old," she gushes during her unprepared acceptance speech. Adding, "As I get older I thank everyone in this room because this is my family." The following week, at the Screen Actors Guild Awards, she takes home the SAG for best actress in a TV movie.
Barrymore, 36, steps out with Will Kopelman, a 33-year-old art consultant, whom she is first spotted dancing with at Hollywood hot spot Music Box. After spending the holidays together in Sun Valley, Idaho, the couple announces their engagement in January. "They are very happy together," a source tells PEOPLE.
With her fiancé at her side, Barrymore is spotted leaving a doctor's office in Los Angeles with a sonogram in-hand. Though she doesn't confirm her pregnancy, the bride-to-be does sport a small bump and is feted with a combined wedding and baby shower in April.
Barrymore, 37, ties the knot with Will Kopelman in an intimate and star-studded ceremony at her Montecito, Calif., home. The expectant, who is five months pregnant with her first child, wears a Chanel gown as she walked down the aisle in front of guests including Camreon Diaz, Jimmy Fallon and Reese Witherspoon. "The day was perfect," the bride tells PEOPLE. "Everyone we love and care about was there. It was as fun and meaningful as we ever could have hoped."
The actress and Kopelman celebrate the birth of their first child, daughter Olive, who is "healthy, happy and welcomed by the whole family," the couple tells PEOPLE in a statement. "It's like the biggest crush I've ever had in my life!" Barrymore later says, introducing her daughter in a December PEOPLE cover story. "You have the highest highs and yet you're facing the biggest fear of, 'How do I keep someone alive?'"
A little over a year after the birth of daughter Olive, Barrymore announces she and husband Kopelman are expecting their second child – a girl. "When I found out I was overjoyed. It always feels so surreal, it's incredible," she gushes to PEOPLE. "You're so lucky to get to do it. It's such a miracle. I just felt really lucky."
And baby makes four! "Happy to announce that today we are the proud parents of our second daughter, Frankie Barrymore Kopelman," the actress and her art consultant husband tell PEOPLE in a statement. "Olive has a new little sister, and everyone is healthy and happy!"
BIOGRAPHY (top to bottom): HBO; Kevin Mazur/Wireimage; Darren Michaels/Mandate Pictures; NBC/AP; Trovarelli/AKM Images; Bruja/Juan Sharma/Pacific Coast News; Dave Spencer/Splash News Online; Steve Granitz/Wireimage