Born and raised in Sudbury, Ont. Now lives just outside Toronto.
Besides hosting a show that speaks to nearly a million listeners each week and is also heard on WBEZ in Chicago, O’Reilly’s full-time job is actually with Pirate Radio and Television, a post-audio production company he co-founded with Rick Shurman in 1990. The half-hour, freewheeling radio show about the business of advertising is actually researched and written in “stolen moments”—on O’Reilly’s two-hour commute to Toronto, on weekends, between recording sessions—yet each episode takes at least 45 hours to produce. Past projects for Pirate Radio include the sound and voiceover direction for the Goodyear/Fountain Tire TV and radio campaigns for the past 20 years; directing Kiefer Sutherland on all the Ford spots, Jeff Bridges on the Canadian Hyundai commercials and, most recently, George Clooney, when he was the voice of Budweiser in the U.S. Every year, you can bank on Pirate’s work being viewed during the Super Bowl for which it collaborates on three or four American TV commercials, plus several for Canadian companies.
Days spent on the road
On average, six plane trips a month— usually between Vancouver and [Pirate’s] eight recording studios in Toronto and New York. But I am like George Clooney's character in Up in the Air; I have it down to a science. I am a Nexus cardholder, so I don’t spend any time in lines and zoom through customs. I put my iris up to a machine and it says, “Hello Terrance, have a nice trip.” And I usually do.
Best restaurant to impress a client
Veritas Local Fare in Toronto has a great feel, and the menu is very unusual and interesting, with lots of organic dishes. It has a nice outside patio in the summer, and it is a favourite spot for the ad industry, so lots of familiar faces in the room. If it was less formal, I’d take them to the Patrician Grill, just down the street from our studio. It’s bacon and eggs on toast and pancakes, and I love the guys who work there.
I take only a carry-on. I wear a jacket and jeans and roll everything else in my suitcase. To me, space is the enemy. You want to plug every bit of space because once things shift, they wrinkle. Sometimes I bring stuff I don’t even need like extra socks so nothing will move if it tips upside down. If I’ve done a good job, I can open my suitcase and walk onto a stage. And never buy black luggage—90 per cent of luggage is black. Finding it on a carousel is impossible. Mine is silver.
Favourite New York hotel
I like the Bowery Hotel, which is kind of close to our office. It’s full of atmosphere, it’s small and you don’t need a Sherpa and a map to find your room. Paul McCartney and Nancy Shevell just had their American wedding reception there in October.
Favourite seat on a plane
An aisle. Always. You never have to bug your seatmate by crawling over him, and you can depart the plane quickly.
Valet service. I always use the valet service at [Toronto’s] Pearson Airport. I just drop off my truck and don’t have to deal with a 25-minute sweaty hunt for a parking spot. When I return, my car is parked at the door waiting for me. They’ll even wax your car while you’re away. Love that!
Favourite family holidays
Two years ago, I took my girls, wife and parents to Italy where we rented a house and fell into a great routine. We’d go for a swim in the morning, have breakfast together and go into town for lunch, come back for a siesta, explore a bit and then have a late dinner. I love watching my daughters discover the world. That’s one of the best parts of being a dad. We also had a great time in Vegas (I think the level of service in Vegas is amongst the best in the world), going to see shows where there’s not a bad seat in the house.
One moment that changed your career (OK, two)
Starring in an ad on the Sudbury set of Romper Room as a four-year-old. But I really saw my future at Ryerson [in Toronto] where I studied radio and television arts—that’s when I discovered I wanted to be a copywriter. Sure, there are deadlines that will kill you. And I had hair when I started. But the puzzle of marketing hasn’t gone away and it’s what I love. Why isn’t a campaign working? What has to change for it to succeed? I love the machinations of that puzzle.