1988–93: Career beginnings
Aniston worked in Off-Broadway productions such as For Dear Life and Dancing on Checker's Grave, and supported herself with several part-time jobs, which included working as a telemarketer, waitress, and bike messenger. In 1989, Aniston appeared on The Howard Stern Show, as a spokesmodel for Nutrisystem. That year, Aniston moved back to Los Angeles.Aniston was cast in her first television role in 1990, starring as a regular on the short-lived series Molloy. She then co-starred in Ferris Bueller, a television adaptation of the movie Ferris Bueller's Day Off (1986), and like Molloy also quickly canceled. Aniston then appeared in two more failed television comedy series, The Edge and Muddling Through. Other roles included the horror film Leprechaun (1993), the TV movie Camp Cucamonga(1990), and guest roles on Quantum Leap, Herman's Head, and Burke's Law.
1994–02: Television breakthrough and rising film career
Depressed over her four unsuccessful television shows, Aniston approached Warren Littlefield at a Los Angeles gas station asking for reassurance about her career. The head of NBC entertainment encouraged Aniston to continue acting, and a few months later helped cast her for Friends, a sitcom that was set to debut on NBC's 1994–1995 fall lineup. The producers of the show originally wanted Aniston to audition for the role of Monica Geller, but Courteney Cox was considered to be better suited to the role. Thus, Aniston was cast as Rachel Green. She was also offered a spot as a featured player onSaturday Night Live, but turned it down to do Friends. She played the character of Rachel from 1994 until the show ended in 2004.The program was successful and Aniston, along with her co-stars, gained world-wide reputation among television viewers. Aniston received a salary of US$1 million per episode for the last two seasons of Friends, as well as five Emmy nominations (two for Supporting Actress, three for Lead Actress), including a win for Outstanding Lead Actress in a Comedy Series. She was also nominated for two Golden Globe Awards and won, in 2003, the Golden Globe Award for Best Actress – Television Series Musical or Comedy. According to the Guinness World Book of Records (2005), Aniston (along with her female costars) became the highest paid TV actress of all time with her US$1 million-per-episode paycheck for the tenth season of Friends. Her relationship with Ross Geller, portrayed by David Schwimmer in the show was widely popular among audiences and the couple were frequently voted as TV's favorite couple by polls and magazines.
Following a four-year hiatus from cinema, Aniston returned to film work in 1996, when she performed in the ensemble cast of the independent films She's the One (1996), and Dream for an Insomniac (1998). Aniston's first starring vehicle was the film Picture Perfect (1997), in which she starred opposite Kevin Bacon and Jay Mohr. While the film received mixed reviews, Aniston's performance was more warmly received, with many critics suggesting that she had screen presence. She starred in the cult film Office Space (1999) for director Mike Judge. She appeared in The Object of My Affection (1998), a comedy-drama about a woman who falls for a gay man (played by Paul Rudd).
She gained critical acclaim for her performance in the low-budget film The Good Girl (2002), playing an unglamorous cashier who cheats on her husband. The latter film opened in relatively few theaters – under 700 in total – taking US$14 million at the U.S. box office. In 2002, film critic Roger Ebert declared the role as her breakthrough film, stating that, "after languishing in a series of overlooked movies that ranged from the entertaining Office Space to the disposable Picture Perfect(1997), Jennifer Aniston has at last decisively broken with her "Friends" image in an independent film of satiric fire and emotional turmoil. It will no longer be possible to consider her in the same way."