Flockhart was cast in the lead role of Ally McBeal in the Fox television series of the same name. This marked a turning point in her career and catapulted her to mainstream fame.

The series 'Ally McBeal' became a massive hit, and Flockhart's portrayal of the quirky and neurotic lawyer earned her critical acclaim, including a Golden Globe Award and three Screen Actors Guild Awards. The show was a pop culture phenomenon.

During the run of 'Ally McBeal', Flockhart faced intense media scrutiny regarding her weight and appearance. She became the subject of frequent tabloid speculation about anorexia nervosa, but publicly denied these accusations, attributing her thinness to stress and work.

Calista Flockhart won the Golden Globe Award for Best Actress – Television Series Musical or Comedy for her role as Ally McBeal, acknowledging the show's cultural impact and the actress's own exceptional work.

After five successful seasons, 'Ally McBeal' aired its series finale, marking the end of an era for both the show and Flockhart's career. The finale was a significant media event, reflecting the series' lasting impact on television and popular culture.