She attended Booker T. Washington High School for the Performing and Visual Arts[3] in Dallas, and later studied at Southern Methodist University[4] until she joined a band and decided to focus on songwriting.

In 1985, Brickell was invited to sing one night with friends from her high school in a local folk rock group, New Bohemians.

Their 1988 debut album, Shooting Rubberbands at the Stars, became a critical and commercial success, including the Top Ten single "What I Am".

Her version of Bob Dylan's "A Hard Rain's a-Gonna Fall" is featured on the film's soundtrack.

The video for Picture Perfect Morning's "Good Times" was included as part of the multimedia samples featured on Microsoft's Windows 95 Companion CD-ROM.

[11] In 1992, she worked with producer Bob Wiseman in New York and Toronto on a collection of songs, utilizing a wind ensemble, unusual keyboards, and Ron Sexsmith.

In 2023, Brickell became the founding vocalist of new band Heavy MakeUp, alongside brass player CJ Camerieri and trumpeter Trever Hagen.

Brickell was performing "What I Am"[23][24] on NBC's Saturday Night Live on November 5, 1988, when she noticed Simon standing in front of the cameraman.