In the mid-1970s, Shydner went to open mic nights at local coffeehouses, and began opening for bands in Washington, D.C. and New York City. In 1982, he brought his act to Los Angeles. Slowly he started getting called in to audition for casting Directors. Shydner studied acting for about four years, and landed a regular role on Married... with Children.
As a stand-up Comedian, Shydner appeared on The Tonight Show Starring Johnny Carson, Late Night with David Letterman and The Tonight Show with Jay Leno numerous times. He performed a HBO half-hour special called One Night Stand, as well as was a guest on Comics Unleashed. Aside from performing stand-up, Ritch, along with Comedian Mark Schiff, compiled stories of comedians on the road in a book called I Killed (2006).
Shydner was featured in the 2010 documentary I Am Comic, in which he traveled around the country interviewing various comedians, a process that ultimately led to his return to stand-up by going on the stage again after 13 years of retirement.