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  • Writer's pictureDavid Reuben

Simon Rakoff

His act is well crafted and thought provoking delivered with the smoothness of a veteran and the enthusiasm of a newcomer.

46 Years In the Game

Marla Lukofsky - Canadian Comedy Legend remembers:


“I first met Simon Rakoff back in 1978 at the original Yuk Yuk’s at the Bay Street location. I was headlining and saw Simon standing at the back of the room along with the other comics. He was relatively new to the scene back then but was clearly devoted to learning and expanding his new act. Soon he got to do opening and middle spots as well as MCing. He was making his mark.


Over time, Simon became a great writer and stand-up comic honing his act with clever, witty and intelligent material. My most recent gig with him was when we did a show together at the Al Green Theatre hosted by David Gale discussing humor and should there be a limit as to what we can get away with as humorists. Can’t recall Simon’s answer but I know one thing… he’s never short of opinions.

To me, that young lad grew into a man, a father and a great headlining comedian before my eyes. Bravo and Congrats to Simon Rakoff, comic of the week.

Always a pleasure to work with and to talk to.”

David Reuben (the author) was lucky enough to recently have lunch with Mr. Simon Rakoff at his home in Midtown Toronto... I first saw Simon perform at the original Yuk Yuk’s on Bay Steet in Toronto in 1978. I was in my first year of University and Simon was just starting his 46-year journey in comedy.

When I stared performing at Yuk Yuk’s on Bay Street Simon was already one of the most requested hosts in the business and becoming a headlining comic. Over the years our careers went in different directions and we would run into each other from time to time. We had so many friends in common as the Canadian Comedy Community is small and tight knit community.

In recent years I was lucky enough to see Simon at various events and shows, I find him to be friendly, extremely intelligent, brilliantly funny. According to his friend and fellow comic Evan Carter; “Simon has a rapier-like wit both on and off stage. His material is has grown with him and is very relatable to the audience.”

Ms. Glenda Fordham, Yuk Yuk’s Booking Manager 1981 to 1985, remembers; “Simon Rakoff was very easy to work with, professional, and an excellent host.”


Close friend and fellow comic Thomas Calnam first met Simon Rakoff 14 years ago at the Spirits Wednesday Night Comedy Show. Over the last five years they have been doing shows together at Absolute Comedy in Toronto and road gigs together.  Thomas says, “Simon is a nice man, very generous with his time to younger comics. Simon works hard, is a great writer, has a love for stand-up comedy, and is fabulous at the transition from crowd work to a written joke.”

Simon Rakoff was born in South Africa and immigrated to Montreal when he was 1-year old with his parents Vivian and Gina. In 1967, the Rakoff family relocated to Toronto. Mr. Rakoff is the oldest of three children, the late David Rakoff and Sister Ruth Rakoff. The Rakoff children were very close growing up.

“My mother was always funny but a very tough laugh. My dad made silly jokes but laughed a lot. My sister and brother were also funny, and we did a lot of shtick growing up. My late brother went on to become a world-renowned humorist and was probably the smartest person I ever knew along with being one of the funniest.”

 Both Simon’s parents were doctors and his brother and sister are accomplished in their chosen fields.

“As you can imagine, two doctor parents were never thrilled with their comedian son’s choice but, I think, over time, they grew to at least accept it. My gift of gab and analytical mind made them hopeful I might choose law which is at least lucrative, but I always say 0- I’m smart enough to be a lawyer and smart enough NOT to be a lawyer.”

“Thing is that intelligence is a gift but I lack other keys to success in the “straight” world like motivation and ambition. I joke that comedy is not a job, it’s a personality disorder. It’s more the way of looking at life and the world and stripping away the artifice to reveal what’s actually going on that is the essence of a comic point of view. It also informs life choices. I only ever cared about doing something I enjoyed with my time without much concern for financial security or status which, to me, are illusory anyway. I know people who devoted their time to a company, doing work they disliked who ended up without security anyway.”

Mr. Rakoff has had multiple success throughout his 46 years in the Canadian Comedy Scene and has traveled numerous times across Canadia performing from Newfoundland to Vancouver Island. 

“What surprises me most is that people are very similar in what they care about no matter where I go. There are definitely different characters in different places. I remember playing NFLD for the first time and thinking how funny everyone I encountered was. Why even import comedy here? They don’t haul ice to Nunavut. That said, they loved my act, and I had a blast. Generally speaking, I think the more personal one makes the material, the more universal it is. There is no percentage in trying to guess what the listener will enjoy. Just be yourself and invite them to come along.”


Simon has appeared on numerous Canadian television shows and festivals, including the Winnipeg Comedy Festival and Just for Laughs. He is also a frequent guest on CBC Radio on The Debaters and As It Happens. He is often hired to punch up television and movie scrips. His album 'Surrounded By Idiots’ came out in 2014,

Riotous Rakoff 

Album review by Glenn Sumi – Now Magazine


“The cover of Simon Rakoff’s Surrounded By Idiots shows the comic in full face-palm mode. It and the title sum up his act very well. Rakoff’s the middle-aged Jewish guy who makes fun of the stupidity around him.

Turns out there’s a lot to satirize, starting with the entertainment industry. The opening bit about putting people in witness protection programs in Canadian showbiz so they’ll never be heard of again is razor sharp.

And thanks to his anti-sports rant, I’ll never hear ACC ticket-sellers’ cries of “Who needs Leaf’s tickets?” the same way again.

He’s got solid material about his Jewish heritage, including clever jokes about brises and alcohol, Jesus’ sarcasm and the particular syntax of first-generation Jewish immigrants that makes them sound like Yoda.


But his strongest stuff comes at the end, when he delineates the differences between men and women and showcases his character skills. An extended bit set in caveman times is the final word in Men Are From Mars, Women Are From Venus humour.”


I asked Glenda Fordham, Evan Carter, and Thomas Calnan how has Simon been able to not only survive but thrive in the business of Canadian Comedy for 46 years? All three said that Simon Rakoff still loves to perform, works hard at his craft, and is contemporary and relevant with his material.

As Evan Carter said, "Simon is comfortable in his own skin, he is happy and relaxed on stage and has a great vibe, he still loves the challenge of different audiences, and is still a student of the craft of stand-up comedy and the world around him.”

Mr. Simon Rakoff has his own theory on why he has thrived in the business of Canadian Comedy for all this time.

“It was a very different time. There was no “scene”. There were about a dozen people trying to see if maybe there was enough interest in stand-up to make a life in it. These days, there are hundreds of wannabes and countless open mic nights for people hoping to be comics. Then, newcomers went on after the regular show on Tuesday or Wednesday nights for whatever audience members were willing to stick around. My first set went fantastically well. I was incredibly nervous, but the crowd loved me. I didn’t have another good set for many after that but I knew the feeling from that first one, so I was hooked.”

Simon continues on how the success happened.

“This goes back to my lack of ambition and happiness doing what I love. I think people who get into comedy thinking it’ll be easier than working or that they’ll be a star are unlikely to last because it is extremely demanding and unlikely to pay off big. I still love doing it and getting my laughs and really think I’d be less happy dealing with the pressure of fame.”

I asked Simon about his process on writing jokes and his stage delivery.

“I am essentially myself onstage. Although I suppose a more self-assured version. My jokes just reflect my thought process although I have worked hard to learn the essential skills that make a thought into a joke. It is akin to Judo, in which one leads the listener to expect one outcome as a misdirection to the punchline. Boy - there is nothing less fun or funnier than deconstructing the process of writing jokes.”

“I am always writing because, as I said, it’s how I view everything that happens. I don’t write a new act on purpose. I liken it to the cells in my body. Every seven years, I’m a completely new person but you don’t see the sloughing of the old cells and the growth of the new ones. It just happens organically through constant maintenance.”

I asked Simon Rakoff what his advice is to people thinking about trying Stand-Up Comedy?

“Do it! There is no downside. The worst possible outcome is you bore strangers for a few minutes. The other possibility is they laugh, and you feel a rush that is unlike anything else.”

When not working Mr. Simon Rakoff spends time with his daughter, enjoys cooking, walking, movies, video games, logic puzzles, reading. I am never bored. If anything, I have the opposite problem of trying to quiet my mind so I can get to sleep.


In the future Simon hopes to continue doing what he loves to do which is performing. “If I’m lucky, more of the same. So many of my contemporaries have died, retired or nobody books them. I am grateful to still be on the scene.


After spending time with Simon Rakoff at his home and at a recent gig we did together, I am happy to see that he is still excited to do stand -up comedy, enjoys his family and time off stage. What more can you ask for in life! As Simon said to me, “I am a lucky man.”

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