- Schindler's List tops the Broadcast Film Critics Association list of the top films of the 1990s. Saving Private Ryan places second, with L.A. Confidential in third. Rounding out the top five are Forrest Gump and GoodFellas.
- Michael Douglas, 55, proposes to Catherine Zeta-Jones, 30, at his Aspen home. They plan to marry sometime this year, but no date has been set. Douglas recently divorced his wife of 22 years, Diandra.
- The final numbers are in, and 1999 emerged as a record-breaking year at the box office. Indeed, moviegoers spent $7.46 billion on movie tickets, an 8.5% increase over 1998. Star Wars: Episode 1 -- The Phantom Menace led the way, taking in $430 million. The Sixth Sense followed with a $276 million haul. For a list of the top 100 grossing films of 1999, see Exhibitor Relations' Top Films.
- Ted Turner and Jane Fonda announce they are temporarily separating after nine years of marriage.
- The Sixth Sense cleans up at the People's Choice Awards, winning both Favorite Motion Picture and Favorite Dramatic Motion Picture. Bruce Willis takes home the Best Actor in a Drama Award. Big Daddy earns the Favorite Comedy award, and its star, Adam Sandler, wins the top acting prize in a comedy. NBC prevails in the television awards, winning both drama and comedy nods for ER and Friends, respectively.
- In the biggest merger in the country's history, America Online agrees to buy Time Warner, the nation's largest traditional media company, for $165 billion. The mega-deal reflects the growing dominance of the Internet in areas including publishing, music, film, and broadcasting. It also serves to validate the Internet, proving that the Web is likely here to stay and somewhat justifying the value of Internet companies that have yet to turn a profit but are worth billions on paper.
- Melissa Etheridge and her partner, Julie Cypher, reveal in Rolling Stone magazine that David Crosby is the father of their two children, 3-year-old daughter, Bailey, and 1-year-old son, Beckett. Cypher, who was artificially inseminated, gave birth to the children. “We just got so tired of this secret,” said Etheridge. “It wears you out. And keeping this big secret goes against how we are choosing to live our lives — very openly.”
- Mr. Blackwell's annual list of Worst-Dressed Women is out, and Cher leads the pack. She's followed by Celine Dion, Queen Elizabeth, Martha Stewart, Fiona Apple, Sarah Jessica Parker, Jennifer Aniston, Cameron Diaz, and the Dixie Chicks. In releasing his list for the 40th time, Blackwell said, “Many of the fashion-challenged women on this year's list are fabulous talents. But when it comes to choosing a wardrobe, they seem to have entered the world of bad taste — no exit in sight.”
- Marc Davis, an animator who was one of the original — and most talented — Disney cartoonists, dies at age 86. He was known for his skill in drawing female characters. He designs include Cinderella, Maleficient, Tinker Bell, and Cruella DeVil. Later in his career, he designed theme-parks rides at Disneyland and Disney World.
- Hillary Clinton appears on David Letterman's Late Show, coming off as a seasoned politician and celebrity. Host Letterman lobs softball questions at her and gives her a “pop” quiz on New York, though she had seen the questions in advance. The episode earned the show its highest ratings in six years.
- Late Show host David Letterman has emergency quintuple bypass surgery. He's expected to make a full recovery.
- Kenneth Branagh wins Britain's prestigious Gielgud Award, becoming the youngest actor to ever win the honor, which recognizes actors who tirelessly preserve the Shakespeare tradition. Past winners include Ian McKellen and Derek Jacobi.
- Michael J. Fox announces he's leaving Spin City at the end of the 1999–2000 television season to lobby on behalf of Parkinson's disease, with which he was diagnosed in 1991.
- Gurinder Chadha's Thanksgiving saga, What's Cooking?, starring Mercedes Ruehl, Alfre Woodard, Kyra Sedgwick, and Julianna Margulies, opens the 2000 Sundance Film Festival. What's Cooking? is one of several women-helmed films to debut at the fest. In fact, 26 percent of the films were directed by women.
- Cable stations, notably HBO, dominate the 57th Annual Golden Globe Awards, winning top honors in the major categories. The Sopranos takes best drama series, best actor (James Gandolfini), best actress (Edie Falco), and best supporting actress (Nancy Marchand). Sex and the City garners the award for best comedy series, and the show's star, Sarah Jessica Parker, is named best actress in a comedy. Michael J. Fox, who days earlier announced he's leaving Spin City to help in the fight for a cure for Parkinson's disease, earns his third consecutive best actor award. For a full list of winners, see Golden Globe Winners.
- Fox announces that both Party of Five and Beverly Hills, 90201 will end after the current television season.
- Catherine Zeta-Jones and Michael Douglas, who got engaged on New Year's Day, announce that the couple are expecting their first child in the summer. It's the first child for Zeta-Jones; Douglas has a son, Cameron, 20, from his first marriage.
- The 2000 Sundance Film Festival, informally dubbed the Year of the Woman, closes, with two films sharing the Grand Jury Prize for top dramatic film. Karyn Kusama's Girlfight, about a teenage girl from Brooklyn with a knack for throwing a punch, ties with Kenneth Lonergan's You Can Count on Me, a film about siblings from a small town.