After meeting him on the set of The Player, a barefoot 25-year-old Roberts marries country crooner Lyle Lovett, 35, in rural Marion, Ind., while she is on leave from filming The Pelican Brief with Denzel Washington in Washington, D.C., and Lovett is between concerts on a summer tour. The pair divorce amicably after 21 months.
Roberts appears on an episode of Friends. A few weeks before the show airs, she is spotted in L.A. with Matthew Perry, whom she dates briefly. The following year, her romantic comedy My Best Friend’s Wedding becomes a box office hit, making $127 million domestically.
In New York shooting Stepmom (which she coproduced with friend and costar Susan Sarandon), Roberts spots Law & Order actor Benjamin Bratt at Raoul's restaurant and orchestrates an introduction. "I realized immediately that he is someone who will always challenge me in that great way that keeps you moving forward," Roberts tells McCall's in 2000. "[He] is all a girl could ever ask for."
Right before appearing on her second Most Beautiful PEOPLE cover, Roberts first meets cameraman (and future husband) Danny Moder while filming The Mexican. Though both are involved (Roberts is still dating Bratt and Moder is married to makeup artist Vera Steimberg), the two become fast friends.
Roberts wins the Best Actress Oscar for her role as a spunky legal secretary in Erin Brockovich. "I love the world!" she screams during a giggly acceptance speech.
After nearly four years, Roberts and Bratt quietly end their very public romance. While friends blamed their hectic schedules for the split, Bratt would later express his discomfort with her fame in a Vanity Fair interview: "It's like a fly that won’t leave you alone, it's that mosquito that buzzes in your ear when you’re trying to sleep at night."
Steven Soderbergh's remake of Ocean's Eleven – in which Roberts shines in an all-star cast including George Clooney, Brad Pitt and Matt Damon – hits theaters, raking in almost $40 million its first weekend. She will also appear in the sequel Ocean's Twelve in 2004, carefully disguising her first pregnancy.
After a year and a half of dating, Roberts and Moder stage a surprise midnight wedding at Roberts' Taos ranch. Roberts wears a simple pink cotton halter dress during the 20-minute ceremony, which had no bridesmaids or groomsmen.
Roberts, the first woman to break into the $20-million-per-film club (after Erin Brockovich), charges full price to join the cast of Mona Lisa Smile, cementing her status as the highest paid actress at that time in Hollywood.
Roberts gives birth to twins Phinnaeus Walter and Hazel Patricia in L.A. Though they have to remain at Cedars-Sinai Hospital for eight days after arriving prematurely (and weighing about 5 lbs. each), they join mom and dad at home December 6, PEOPLE reports. "The babies are healthy," a family friend tells the magazine. "They're doing great."
BIOGRAPHY (top to bottom): PETER NASH/Picol; Warner Bros./Everett; EVAN AGOSTINI/Getty; Sam Mircovich/REUTERS/Landov; SANTE D'ORAZIO/AP