- Running for Democratic Nomination to U.S. Congress from the First Congressional District of Iowa in 2016. He withdrew from that election to run instead for the Iowa House of Representatives, an election he lost.
- Founding member of the Practical Theater Company, the Howard Street comedy ensemble in the John Lennon Theater that included Brad Hall and Julia Louis-Dreyfus, both Northwestern graduates.
- Graduated from Northwestern University in 1981.
- Among Gary's closest friends at Northwestern was writer Allison Burnett.
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