Ritchie Montgomery: A man of many faces

• During his career, the Mississippi-native has acted in close to 200 plays, commercials, television shows, and feature films.

Ritchie Montgomery was born just 16 miles north of Natchez in Fayette, Mississippi, but he was destined to go to Hollywood.

“I left this area as a 25-year-old full of hopes and dreams.”

He spent the next thirty years in Los Angeles, imitating others, creating characters, and playing a role in countless feature films and television shows. 

“I figured out that I was funny while attending Sewanee Military Academy in Tennessee.”

Ritchie recalls his art teacher, Colonel Moore, who recognized that Ritchie had a creative mind.

“He encouraged me to take art classes, but I couldn’t paint or sculpt at all.” But Moore took an interest in Ritchie, and they talked a lot.

“Colonel Moore suggested we put together some skits to entertain the school. I did parodies of the alcoholic bus driver who managed to get us to sporting events and back to the school without killing us all.”

The school’s janitor, who was often the butt of jokes and bullying by other students, became a friend of sorts to Ritchie.

“We talked a lot, and he was always kind. He and his family lived in a cave. I told him I was going to do a skit about him and asked him to come. He declined but asked if I would wear his boots.” 

Ritchie opened and closed the show with his skits, and when he looked into the audience at the end, he saw the janitor.

“He said it was one of the most exciting moments of his life. I knew then that my life had changed. I understood the power of the performing arts and the effect I could have on people.”

Ritchie attended Ole Miss before transferring to the University of Southern Mississippi, where he earned a bachelor’s degree in fine arts.

Before heading to Los Angeles, Ritchie managed to get his Screen Actors Guild (SAG) card due to his role in Freedom Road, filmed in Natchez in 1977.

“I was a production assistant, and they recruited me to play a Union soldier. I was also the assistant to Mohammed Ali in that film, and we became friends.”

By 2010, Ritchie was ready for a change. He had lived the hustle-and-bustle life in Los Angeles for three decades and longed for a quieter life. When he was called to work on The Help, he packed up and drove across the country to Greenville, Mississippi.

“The first thing they asked me was if I could drive a 1940s bus. I told them I could drive anything from a covered wagon to a Zamboni, which is true!”

During his career, Ritchie has acted in close to 200 plays, commercials, television shows, and feature films. He also did a stint at The Comedy Store in Los Angeles. 

With the film industry taking off in Natchez, Ritchie has returned to his roots.

“I love being back in Natchez. My friends in Los Angeles don’t believe me when I tell them I can walk to work!”