In her early career she performed in various comedy clubs in the NYC area including the legendary Catch a Rising Star and Who's on First, both now shuttered.
She has been featured in over 2 dozen television shows, including Showtime's Comedy All Stars 6 with Don Rickles and Politically Incorrect with Bill Maher.
The San Antonio Times called Montgomery "one of the pioneering female comics of the modern era."
[2][3] During her time in Las Vegas, Montgomery wrote and performed her one-woman show Confessions of a PT&A Mom in various theatres.
That year she was one of 10 contestants on Nick at Nite's The Search for the Funniest Mom in America reality competition.