- In an interview with the British magazine Hello!, Minnie Driver announces that she and actor Josh Brolin are engaged. Driver has had a string of very public relationships and breakups; the most high-profile was her fling with Goodwill Hunting co-star, Matt Damon. Brolin is the son of actor James Brolin, who recently married Barbra Streisand.
- Pierce Brosnan announces plans to marry Keely Shaye Smith, his longtime girlfriend and the mother of his 2-year-old son. No date has been set.
- Michael Jackson announces that he and his wife, Debbie Rowe, are divorcing. The couple has been married for three years and has two children. It is Jackson's second divorce. He was briefy married to Lisa Marie Presley. Rowe and Jackson, while still legally married, have been living apart essentially since they married. Jackson lives with the two children at his Neverland ranch in Santa Barbara, Calif., and she lives in Los Angeles. The two promise to remain “good friends.”
- TV Guide releases its list of the top 50 television characters of all time. Danny De Vito's Louie De Palma from Taxi tops the list. Rounding out the top five are Ed Norton, from The Honeymooners, Lucy Ricardo from I Love Lucy, Fonzie, Happy Days, and Archie Bunker of All in the Family.
- Xena star and cult hero Lucy Lawless welcomes her second child, 8-pound, 13-ounce Julius Robert Bay Tapert. She is married to Xena producer Robert Tapert. She has a daughter, Daisy, from a previous marriage.
- Steven Spielberg garners the Film Director and Humanitarian awards at the annual GQ Awards ceremony in New York. He was cited for the 1998 film Saving Private Ryan. Tom Hanks, the film's star, was also honored with a GQ Actor Award. The television award went to Michael J. Fox, Kevin Spacey wins the Theater Award, and Calvin Klein takes the Fashion Award.
- Sandra Rosas, the wife of Los Losbos frontman Cesar Rosas is kidnapped. Her half-brother, Gabriel Gomez, is arrested on Oct. 24 in connection with her disappearance.
- During a training flight, Harrison Ford crash-lands his helicopter about 60 miles outside of Los Angeles. No one was injured.
- Actor Matthew McConaughey is arrested in Austin, Texas, on charges of possession of marijuana, possession of drug paraphernalia, and resisting transport. Police, responding to a noise complaint, found the actor naked, playing the bongos, and surrounded by drug paraphernalia.
- The band Hole confirms that bassist Melissa Auf Der Maur has left the band. No reason was given for her departure. The band, led by Courtney Love, is looking for a replacement.