What If (2013)
Can a man and woman really be just friends? What If manages to breathe new life into a familiar cinematic trope thanks to its charming stars, witty dialogue by Canadian screenwriter Elan Mastai, and the romantic backdrop of Toronto. Like Scott Pilgrim vs. the World, What If is never subtle about the fact that it’s set in Toronto. But instead of popular attractions, Daniel Radcliffe and Zoe Kazan’s ultra-hip characters meet and fall in love in lesser-known locations like the George Street Diner, Rooster Coffee House, Riverdale Park and the Royal Cinema. There’s so much Toronto in What If that you’re bound to fall in love with the city all over again.
Based on the 1959 novel by Mordecai Richler and starring Richard Dreyfuss, The Apprenticeship of Duddy Kravitz follows the titular character as he tries to scheme his way out the poor Jewish community of 1950s Montréal. Saint Urban Street plays a prominent role in the film, as does Wilensky’s, a popular lunch counter first opened in 1932 that you can still visit today. Highly recommended is the Wilensky Special: a sandwich of all-beef salami and bologna, Swiss cheese and mustard pressed between two slices of yellow bread—a meal that Travel + Leisure declared one of the best sandwiches in the world.