James Van Der Beek As Simon Tremblay
Some of the best How I Met Your Mother jokes over the years have been mocking Robin’s home country and her past. There have been plenty of jabs at Canada and even more laughs from her prior life as a teen pop sensation. One of the most significant parts of Robin’s youth though is her first boyfriend, Simon Tremblay, who is played by James Van Der Beek.
When they were young and in love, Simon had a band called The Foreskins. Robin was so head over heels from him that she lugged his equipment around for him after shows. To Robin’s dismay, Simon dumped her in favor of Louise Marsh, whose parents had just bought a pool. Years later, Simon comes to visit and he hasn’t changed at all.
While it’s funny to watch Van Der Beek play the young Simon, he’s truly great as the manchild Simon, still thinking that his job at the water slide park is more important than anyone else’s. He briefly gets back together with Robin, but ultimately he has to let her go again. After all, Louise Marsh’s parents did just put in a Jacuzzi.