Early career success

Since child, Lindsay Lohan began her career with Ford Models at age three, but found little work as a fashion model. She persisted and eventually appeared in more than 100 print-ads for companies like Toys "R" Us. She also modeled for Calvin Klein Kids (usually with siblings Michael and Ali) and Abercrombie Kids.

As a her first auditions for television work did not go well; by the time she tried out for a Duncan Hines commercial, she told her mother that she would give up if she did not get the job. She was hired, and went on to appear in over 60 commercials, including a Jell-O spot with Bill Cosby. Her ad work led to roles in soap operas, and she was already considered a show-business veteran in 1996 when she landed the role of Alexandra "Alli" Fowler on Another World, "where she delivered more dialogue than any other 10-year-old in daytime serials" of the time.

Then Lindsay Lohan gave up Another World for the big screen when director Nancy Meyers cast her to play the dual roles of the estranged twin sisters who try to reunite their long-divorced parents (Dennis Quaid and Natasha Richardson) in the 1998 remake of The Parent Trap. Trap was well-received for a family comedy, bringing in US$92 million worldwide. Film critic Janet Maslin found Lohan's dual performances so forceful "that she seems to have been taking shy violet lessons from Sharon Stone." Critic Kenneth Turan called Lohan "the soul of this film as much as Hayley Mills was of the original, and … she is more adept than her predecessor at creating two distinct personalities".

Finally Lindsay Lohan starred in two original television movies, Life-Size (2000) (with Tyra Banks) and Get a Clue (2002). She also played Bette Midler's daughter in the first episode of the short-lived series, Bette (2000), but Lohan, then 14, quit when the production moved from New York to Los Angeles. In 2001, she hosted the ABC-TV commercial series commemorating Walt Disney's 100th birthday during a rebroadcast of The Parent Trap.