With well over 250 acting credits to his name, Stephen Tobolowsky is one of our preeminent “where do I know that guy from?” actors, a title he warmly embraces. On top of that, he has a reputation as one of the nicest guys in Hollywood, and has become known as a bit of a master storyteller. Though he has graced us with a Random Roles interview once before, we were itching to sit down with the actor again to touch on his busy—and harrowing—past decade of work and to revisit more of the beloved roles that have gone on to define his career. Luckily, the surprise renewal of One Day At A Time at Pop TV provided us with the perfect opportunity, so we carved some time out of Tobolowsky’s rounds at the winter Television Critics Association press tour to go long on his illustrious career. We touched on the universal appeal of One Day At A Time, how he balances multiple recurring TV roles at once, and found out how his guest stints on Glee and Community helped him through a particularly rough time. Tobolowsky also explained how an unconventional audition helped him book Silicon Valley, and why he still claims Memento’s Sammy Jankis was the hardest he ever worked for a role.