He was best known as the first African-American clown to perform in Ringling Bros. and Barnum & Bailey Circus,[1][2][3][4][5][6][7] though he spent only a year of his career doing so.

[7] He said of the experience: "Especially being of color, I am always figuring out a way to survive in the world and in the theater...I grew up in Tallahassee, Florida in the 50s where people were still being lynched".

After graduating from Florida A&M University in 1968, Montgomery studied at Ringling Bros. and Barnum & Bailey Clown College, the first year of the school's existence.

He did not want to appear in white face, and with the agreement of circus managers he applied a more scaled down clown make up.

[15] In theater, Montgomery staged Spunk (1990) and Broadway's [19]production of Mule Bone (1991), as well as Digging Eleven, I Ain’t Yo Uncle: The New Jack Revisionist Uncle Tom's Cabin, The Colored Museum and …Love, Langston at Hartford Stage, where he also served for 2 years as an associate artistic director.

Montgomery previously appeared in George C. Wolfe's original productions of Back Alley Tales,[20] Spunk (he played a pimp)[11] and The Colored Museum ("a series of satirical sketches about black American history" playing various characters, including "Walter-Lee-Beau-Willy, a purposely stereotypical black man" and "Miss Roj...a transvestite in white go-go boots and orange patio pants").

There was, quite simply, no space, no distance, no on-and-off switch to Reggie and his artistry.”[22] In 2001, he portrayed James Baldwin in Wesley Brown's A Prophet Among Them (his final acting credit).

[23][24] In 2000, Montgomery directed Suzzanne Douglas in Lady Day at the Emerson Bar and Grill, at the George Street Playhouse in New Brunswick, NJ.

He previously worked with Douglas in an Actors Studio production of The Obeah Man, a musical adaptation of Molière's The Doctor in Spite of Himself.

Montgomery also taught acting at the Alvin Ailey School of Dance and at the American Musical and Dramatic Arts Academy in New York.

And from that very first meeting I knew Reggie was a great artist: A heroic spirit, a subversive jester and a fierce warrior.