He designed a greeting card series with characters who took the shape of musical notes and later published his first cartoon collection, Notable Quotes, in 1981.

In 1984, Steven Hendrickson, entertainment editor for the Antelope Valley Press, Palmdale, California, approached Rubin about writing a daily comic for the paper.

Leigh also enjoys a busy schedule giving thought-provoking and entertaining cartoon presentations at conferences, as well as professional organizations all around the country.

Leigh's first visit as the Cartoonist-in-Residence was in November 2018 where he lectured and taught classes on creativity, and imagination as well as addressing the business aspects of cartooning, branding, and syndication.

[5] On August 25, 2020, Leigh Rubin and Phil Hands, editorial cartoonist for the Wisconsin State Journal performed a live stream event "When Cartoon Worlds Collide: A Twistedly Absurd Mashup of Politics and Comics" hosted by Deadline Club, the New York City chapter of Society of Professional Journalists.