Personal Philanthropy

The Tim Sims Encouragement Fund Award

The Tim Sims Encouragement Fund recognizes and supports promising comedic performers in the early stages of their careers.

The Tim Sims Encouragement Fund was founded by Lindsay Leese and established in 1995 in the spirit and memory of Tim Sims, a well-known comedic performer, writer, director, and charity fund-raiser from Toronto. The Toronto comedy community, Andrew Alexander and The Second City, friends of Tim and the annual fundraising showcases associated with the TSEF have raised the capital for the Fund. The interest generated by the capital makes up the annual cash award.

From 1996-2014, the Fund awarded prize money totalling $65,000 to young comedians in the early stages of their careers.  The award was presented at the annual Cream of Comedy award show at Second City, which featured comedy performances by five outstanding jury-selected Tim Sims Award Nominees.   The award was one of recognition and not designated for any purpose other than the recipient’s encouragement.

Beginning in 2015, the $2,500 award is given annually to a graduate of the Comedy Writing and Performance program at the Humber College, School of Creative and Performing Arts and until 2019, to a Conservatory Program Graduate at the Second City Training Program..


2021 Recipient

Humber College's Comedy: Writing and Performance Program

Cassandra DeStellis

Cassandra DeStellis is a writer, comedian, musician, storyteller, dungeon master, and all-around geek. Fresh on the Toronto comedy scene, Cassandra is a recent honours graduate from Humber College's Comedy Writing and Performance program and is eager to get her hands into everything she can. 

While interested in everything from improv to YouTube sketch comedy, the circumstances of the pandemic are now turning Cassandra's attention to refining her written scripts and rewriting most of her stand-up material. Her comedy has been described as a blend of self-deprecation and social commentary, and she is a big believer in teaching through humour. She has performed for FRESH New Comedians Showcase, Replay Storytelling, Humber Nights at Yuk Yuk's, and can be seen popping into various shows around the city.

Prize: $2,500

Past Winners 

News Releases
Cassandra DeStellis Awarded the Tim Sims Encouragement Award   November 22, 2021


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