[2][3][4] The Boston Globe wrote: “Over decades, she’s built a cult following through Boston radio and the New England folk circuit for her uncanny ability, not unlike Tom Rush, to have her audience laughing during one song and silently tearing up with the next.”[2] “If Wheeler never picked up an instrument, she could have easily become a comedian,” said another reviewer.

Because, after the jokes, stories and self-deprecating comments have people rolling in the aisles, she starts singing and her voice is spellbinding.”[5] Born and raised in Timonium, Maryland, Wheeler began playing ukulele and guitar in middle school and writing songs in high school, making up melodies to go with the poems in “The Golden Book of Poetry,” a children's book.

[8] In 1976, Wheeler moved to Providence, Rhode Island, and began playing at folk clubs throughout New England, opening for artists such as Jonathan Edwards, Tom Rush, Jesse Winchester, and Gordon Lightfoot.

Wheeler's next four albums – Driving Home (1993), Mrs. Pinocci's Guitar (1995), Sylvia Hotel (1999), and Defying Gravity (2005) – were produced by the folk-oriented Philo-Rounder Records in Cambridge, Massachusetts.

[3][8] Wheeler's songs have been covered by a number of other artists in addition to Dan Seals and Suzy Bogguss.

They include Kathy Mattea, Sylvia, Garth Brooks, Peter, Paul, and Mary, Bette Midler, Kenny Loggins, Melanie, Holly Near, and D.C.

[11][3] Wheeler released the recording into the public domain to exempt radio stations from paying royalties (it was being played every hour near the high school), and Rounder Records ran a promotional campaign to donate money to the Brady Campaign each time the song was played on Adult Album Alternative radio stations.

[8] Wheeler has toured extensively throughout her career, and her live concerts include both comedic and serious commentary in addition to the songs themselves.

As one reviewer wrote, she “masterfully blends blisteringly on-target observational humor, simple storytelling, gorgeous guitar work, and beautiful, rich songs.”[4] Another commented on her “free-wheeling live concerts” and called Wheeler a “thoughtful, amusing musician and storyteller (and irrepressible social critic)….

[H]er patter is a delicious, folk-flavored blend of Phyllis Diller and Mort Sahl, sometimes puckish, sometimes barbed.”[6] About half of the songs Wheeler performs in concert are not available on any of her albums.

[14][2] In October 2022, her management announced that her forthcoming concerts were cancelled due to hospitalization for mental health challenges.