Jada Pinkett Smith was originally supposed to play Lisa, but was too short for the role (opposite a 6'2" Will Smith), thus leaving Long to take the part. Also, in the second season of the show (episode 8 - "She Ain't Heavy" 1992), Long appeared as Claudia, a love interest of Smith's, alongside Queen Latifah. In 2000, Long auditioned for the role of Alex Munday in Charlie's Angels, but did not get the part because she "looked too sophisticated and too old next to Drew Barrymore." The role was eventually given to Lucy Liu. In 2003, Long joined the cast of the drama Third Watch, where she played NYPD officer Sasha Monroe, continuing until the series finale in 2005. In 2005 and 2006, Long appeared on Everwood, and guest-starred on Boston Legal during its 2006–2007 season. She then starred alongside Michael Vartan and Dylan McDermott in Big Shots from 2007 to 2008.