Arriving in Boston, he co-founded the comedy troupe Slap Happy, along with fellow UMass alum Allan Jacobs.
[1] Joined by Jeff Ernstoff and Jan Kirschner, the group toured the nation and reached over 200 universities,[2] receiving critical praise for performances in Boston, Cambridge and New York City.
[3][4] During the Slap Happy tour, O'Connor participated in a Ford's Theatre production of the Andrew Lloyd Webber musical Joseph and the Amazing Technicolor Dreamcoat.
[8][9][10] Following his appearance in the indie comedy film Terrorists (2004), Mr. O'Connor performed in the 2005 Geva Theatre Center production of the solo play The Race of the Ark Tattoo.
He was married for seven years to actress Jane Brucker, best known for portraying Lisa Houseman in Dirty Dancing (1987); they have a daughter, Sally (born 1989).