Before Ray Romano graced our television sets with Everybody Loves Raymond, he was a hustling stand-up comedian, hoping to break into television like his peers Jerry Seinfeld, Tim Allen, and Rosanne. He followed all the proper steps—performing on late night television, selling out road gigs, and getting featured in HBO comedy specials—but radio silence was all he got from the powers that be. After eleven years as a full-time stand-up, Ray realized, “Maybe this acting thing just isn’t meant to be.” But that’s exactly when he got offered the development deal that would turn into the hit show Everybody Loves Raymond, and make Ray not only the highest paid actor in sitcom history, but one of the most recognized people in the world.

Despite all of his success and fame, Ray dealt with an unexpected identity crisis when Raymond ended. “It took about three months until the void smacked me in the head. It was this sense of, ‘What now? Where’s my passion? Where’s my direction? What am I throwing all my energy into now?’ I had this non-stop creative energy for nine years. And suddenly, I was empty.” But working through the existential void turned out to be a blessing in disguise. It’s what led to the creation of Men of a Certain Age, the show Ray co-wrote with his friend Mike Royce, and it led to a desire to flex his acting muscles in other, more dramatic areas.

Getting people to see him as more than a sitcom actor was difficult, especially after spending nine years in the shoes of one character that was loosely based on himself. “I didn’t want to make everyone forget about my sitcom legacy, because I was proud of it, but my goal was to do what I wanted—and what I wanted was to stick my little dramatic toe in there.” Since he made that decision, he’s evolved into a versatile and relatable dramatic actor with his work in projects like Parenthood, Vinyl, Get Shorty, The Big Sick, and most recently, Paddleton, opposite Mark Duplass.

Ray joins Off Camera to talk about the first and only time he was fired, how he turns real life into a comedic bit, and why it’s so hard for some men to say, “I love you.”