Uptown Magazine

A Rare Pair By Sharilyn Johnson

Just how rare is it to see brothers Simon and David Rakoff on the same bill?

“The only time we ever worked together was at summer camp,” says Simon. “We once sang Cow Cow Boogie.”

The chances of seeing that number revived for Meet The Rakoffs at the Gas Station Theatre on Thursday night are slim to none — as entertaining as it would be — but it’s certain The Rakoff boys will have something similarly funny on offer.

Simon, older by four years, has been doing standup since 1978. He’s a self-proclaimed “grizzled veteran” according to his tongue-in-cheek username on a Toronto comedy messageboard. He doesn’t tour much, preferring to work in the Toronto area so he can spend time with his five-year-old daughter.

David is the author of two popular books: Fraud, a collection of very funny essays, and Don’t Get Too Comfortable, a commentary on American excess. He’s also a journalist, National Public Radio contributor, and actor. His name is attached the most intellectually hip projects: He’s in Capote and the upcoming Strangers With Candy movie, has directed and performed in plays by Amy and David Sedaris, and provided the voice of Thomas Jefferson in the audiobook version of the Daily Show’s America: The Book.

Their lives have a very different pace and style, which of course wasn’t always the case.

“We were close growing up,” David says.

“We were small. We were bookish,” says Simon. “We got along quite well as kids. We spent a lot of time together”.

Clearly, theirs wasn’t the stereotypical brother relationship, characterized by constant bullying.

“We weren’t like that. We were more likely to be putting on a play,” Simon says. He jokes that if anything, it would be the two of them plotting against their sister, Ruth, the middle child of the three.

Both Rakoff boys followed their creative callings in their late teens. Simon started doing standup while he was in high school, and David moved to New York.

“The truth is, we don’t know each other that well as adults. [David] left home at 17 to go to Columbia University and was gone from there,” says Simon. “And by the point he had left home, I had already left, certainly mentally, before then. I had left university and was pursuing my comedy career, which was not, as I say, in the family plan.”

That ‘family plan’ is a gently skirted issue. David rarely mentions his family in interviews or in his work. Simon characterizes his parents as being very funny and a likely source of his comedic inspiration, but as for his decision to be a comedian, Simon will only explain that it’s more acceptable to them now than it was initially.

“I think as time has passed, and I’ve done okay, and they’ve seen the relative unhappiness that can accompany a more secure but less rewarding job, they’ve come to accept, at least, what I do,” he says. “But I think it worries them still. It’s not financially secure, what I do. My brother has done extremely well, so I think that makes them relax and feel good.”

While being funny is a big part of David’s career, the comedy industry isn’t the world he lives in. He says he almost never watches standup, and hasn’t even seen Simon¹s act in many years.

Furthermore, anyone who’s read Fraud might be surprised to see David at a comedy festival. His essay The Best Medicine, about his experience at the US Comedy Arts Festival in Aspen, details his distaste for the self-absorbed nature of such affairs.

“There’s absolutely nothing wrong with a community getting together to be with itself and toast itself. But it was the sense that one got that one was actually attending the League of Nations,” David says.

He doesn’t anticipate a similar level of ego-feeding in Winnipeg, though.

“It doesn’t strike me as being all that self-congratulatory a venue,” he says of our festival. “[Simon] says it’s about the nicest, most congenial atmosphere he¹s ever been in, with incredibly lovely people.”

Indeed, Simon cites his time at the 2004 festival as the most fun he’s ever had, and he¹s looking forward to catching up with colleagues with whom he doesn’t often work.

“For me it’s fun, because after 28 years [in comedy] there¹s a lot of people I know,” he says. “It’s always nice to run into old friends who you hardly ever get to see.”