Lohan began her career with Ford Models at age three and, at a time when blue-eyed blondes were in highest demand, the freckle-faced, auburn-haired child found little work as a
fashion model. She persisted and eventually appeared in more than 100 print ads for
Toys "R" Us. She also modeled for
Calvin Klein Kids (usually with siblings Michael and Ali) and
Abercrombie Kids. Through young adulthood, Lohan was featured in such diverse magazines as
Vogue,
Elle,
Bliss (
UK), Хай Клуб (
High Club,
Bulgaria), and
Blenda (
Japan).
Lohan's 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 Lohan went on to appear in over 60 commercials, including a
Jell-O gelatin 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 ten-year-old in daytime serials" of the time.
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. Hired in 1997 at age 10, Lohan was 11 when filming began in
England and
California (in
Los Angeles and the
Napa Valley). "I left school for eight months," she said. "When I came back, my friends [asked], 'Where'd you go?' I said, 'My family and I went on a long vacation.' Then the movie came out, and they were, like, 'Um, Lindsay? That's you in
Parent Trap,' and I said, 'Oh, yeah. I also did this movie while we were gone.'"
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".
Signed by Disney to a three-film contract, Lohan was offered the role of Penny in
Inspector Gadget but, after seven months' work on
The Parent Trap, she turned it down. Later, she 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.
Following a brief hiatus, Lohan won a lead role in another Disney remake:
Freaky Friday (2003), starring
Jamie Lee Curtis. Through 2005,
Friday was Lohan's biggest commercial film success, earning US$160 million worldwide.