Keenan-Bolger was born in Detroit, Michigan. She appeared as a munchkin in the Madison Square Garden production of the Wizard of Oz at 13 years old opposite Roseanne Barr. She has credits in the national tours of The Will Rogers Follies and The Music Man as well as numerous regional credits and college productions at Oberlin College where she graduated from in 2006 with a BA in Theatre and Gender & Woman's Studies with a minor in Comparative American Studies. In 2008, she performed in a special cabaret alongside her two siblings entitled ³, the first time all three Keenan-Bolgers had performed together on stage in 15 years, to a sold out house. As a playwright she created and wrote the play From the Inside, Out about her own experiences as a self injurer and other stories about "cutting" from hundreds of people whom Keenan-Bolger personally interviewed. Produced by 4th Meal Productions, it was originally performed at Oberlin College and also played at the noted New York International Fringe Festival in August 2008. In 2010 she graduated from CUNY's Applied Theatre graduate school program using theater to educate, activate and facilitate. While there, she produced, directed and performed in ', a devised theatrical project exploring issues of women's experiences in public space. Most notably, she is the co-founder and artistic director of which has produced works such as, ' and . Both plays were written in collaboration with LGBTQIA homeless youth from New York City and presented in a staged reading with the youth performing alongside of Broadway performers. Her company produced two touring devised theatre productions, about gender and sexuality and about the body. They also produced a NY production of about cis women and trans people in the field of engineering. The company also produces the , a video series created by trans ensemble members about trans experiences in order to provide a funny, accessible, educational learning tool for cis and trans people alike. A two-time Point Foundation scholar, Maggie got her MFA at Goddard College in Interdisciplinary Arts in 2014, where her focus was on Political Theatre, LGBTQIA and Feminist Studies. She was invited to the White House by Vice-President Joe Biden as an LGBT Leader of the Next Generation and was profiled in The Advocate's " She has worked for projects such as Bridging the Gap, I LoveFemale Orgasm Program and many arts in education organizations. Maggie is openly queer and also open about being a person with a disability. She has cervical dystonia, a neurological movement disorder and is active in the LGBTQIA and disability theatre and advocacy communities.