In 2005, she starred in the ensemble drama, Edmond alongside Julia Stiles.
In December 2004, she posed for a nude pictorial in Playboy magazine, five months after giving birth.
As a child, she was the "only girl on the baseball team." She spent the majority of the 1990s appearing in lower-budget films and television shows such as Saved by the Bell, television movies, and guest starring in episodes of several television shows such as Married... She later made guest appearances in shows such as Beverly Hills, 90210 (1992), Seinfeld (1993), Lois and Clark (1994) and a guest-arc in Melrose Place (1996).
Her first starring role in a wide theatrical release was Starship Troopers in 1997 for which Richards was nominated for the Blockbuster Entertainment Award for Favorite Female Newcomer. Variety praised Richards' transition from good-girl-type roles to manipulative villainess and the review continued to include her as part of "an ensemble that appears to be enjoying the challenge of offbeat roles and unusual material.
Richards appeared in films such as Valentine (2001), Undercover Brother (2002) and Scary Movie 3 (2003).
In 2003, she made a very brief appearance in the British romantic comedy, Love Actually.
There's not a wrong note struck by the game group of players." Richards was cast as the nuclear physicist Christmas Jones in the 1999 James Bond film The World Is Not Enough (1999).
In 2005, she starred in the short-lived UPN series Sex, Love & Secrets. She has appeared in numerous films, including Starship Troopers (1997), Wild Things (1998), Drop Dead Gorgeous (1999), The World Is Not Enough (1999) as a Bond girl, and in Valentine (2001). Between 20, she was a series regular on the comedy Blue Mountain State. In 1986, she appeared in the Double music video: "The Captain of Her Heart," when she was 15 years old.She played Monica and Ross Geller's cousin on Friends (2001). She graduated in 1989 from El Camino High School in Oceanside, California.Richards posed semi-nude for the July 2006 issue of Jane magazine to raise money for the Clothes Off Our Back Foundation.
Later that year, Richards starred alongside Kirsten Dunst in the beauty pageant satire, Drop Dead Gorgeous.
Richards, playing a spoiled princess, was praised for her performance by Los Angeles Times for being "as rightly nasty as she is pretty." Later that year she appeared in four episodes of Spin City as Jennifer Duncan, a love interest of Charlie Sheen's character.