Defining Success Through Grit, Self-Discipline, Team Work, and a Positive Outlook: Wendy O’Brien ‘88  

From lessons learned in sport, life experiences, and meaningful relationships, Wendy is flourishing as a highly successful freelance casting director and an accomplished Masters level rowing champion. 

Growing up and watching her older brothers, Jamie ’81 and Kevin ’83 at Ridley, in addition to hearing stories from her uncle Doug Dron ’74, Wendy was eager for her turn to become a Ridleian. She spent Grade 9 as a boarder at The Bishop Strachan School in Toronto and vividly remembers crossing off the days on a calendar until she could join Ridley in Grade 10 (the entry year for girls at that time). Although she lived in Fonthill, she convinced her parents to let her board, so she could soak up the complete Ridley experience. “I just wanted to get involved in as much as possible,” she recalls. She felt supported and encouraged to join in new activities, noting that “Ridley was a safe place to fail. The fact that you can get up afterwards is, in itself, a success.”  

While Wendy did not consider herself a natural athlete, she became very involved in rowing. Although she took a short break when she missed the cut for the Junior National team in the summer of 1986, she returned to rowing in her senior year. Over the course of her Ridley career, she won two gold medals in the Women’s Eight, a gold medal in the Women’s Double, and bronze in the Women’s Four at the CSSRA. Rowing for the Ridley Graduate Boat Club, she won gold again in the Intermediate Women’s Pair at the Canadian Henley.  

Following her passion for rowing, Wendy attended the University of Washington in Seattle, renowned for its rowing programme. She lettered every year at university and was named captain of the varsity team, spending many hours competing across the United States. She had her hopes set on competing for the Canadian Olympic team in 1992, but with training remotely in the United States, unfortunately, the stars did not align.  

In 1992, during the final year of her B.A. where she majored in English with a focus on creative writing, Wendy took an internship with a casting company in Seattle. She always had an interest in dramatic arts, as far back as Grade 9 when she auditioned for a few productions in Toronto. While her interests in dramatic arts had taken a back seat during her competitive sports days at Ridley and university, she now had an opportunity to explore this creative side. She made a conscious decision to take a hiatus from rowing during this early career move.  

From her four-month internship, Wendy landed a job in Vancouver, first as an assistant casting director and then as Associate Casting Director for the series The X-Files. She then set out on her own and subsequently cast the TV series, Cold Squad and Highlander. In 1997, loving the creative side of her work, she realized that she would need to move to Los Angeles in order to participate on a larger scale with more exposure and opportunities.   

Fast forward to 2021, and Wendy has a highly successful and busy career as a freelance casting director in Los Angeles, where she lives with her husband and two daughters.  

She returned to row at the highly competitive masters level, training out of three different clubs: California Yacht Club, Long Beach Rowing Association and the Toronto Sculling Club. When she isn’t busy casting for various films and TV series, she is training and competing in rowing regattas across the country. Her list of accomplishments in competition is impressive. At the Head of the Charles Regatta, she has competed in the Women’s Master Eights on countless occasions, winning gold twelve times and setting three-course records, one of which stood for over a decade. This is a race with over 150 competitors, many of them former Olympians, national and/or world champions! In 2017, she won the Royal Henley Masters Regatta, followed by the Masters National Championships in the United States in 2018. Wendy’s focus is on the support and encouragement that comes from the team, noting that “there is always someone better or someone worse than you.” Not surprisingly, Wendy was recognized and inducted into the Ridley Athletic Lives of Distinction at her last class reunion in 2018.   

The self-discipline and hard work that comes from being a highly competitive athlete has helped her to juggle the many aspects of her life and enjoy success. As a freelance casting director, Wendy has been involved with multiple companies such as NBC, ABC, HBOMax, FX and Netflix in a wide range of films and TV series over the years. In 2004, she was nominated for an Emmy Award for her work on the series Carnivale on HBO. She enjoys helping to shape roles and characters as well as challenging norms in terms of diversity and inclusion. When asked about some of the productions she has worked on that stand out for her, she provided the following observations. Casting for The Way Back (Warner Bros. Pictures) with Ben Affleck required finding balance with the subject matter, which was dark, by finding actors who could naturally infuse some humour, and finding kids who could actually play basketball well and act. She is proud of her work for the TV drama series Sons of Anarchy (FX) which was very challenging and for her work on the TV series Dave with Lil Dicky which was a very complicated casting project. She is enjoying working on the 15th season of the sitcom It’s Always Sunny in Philadelphia, noting that, “It’s a really fun series to be involved with.” Other projects have included Mr. Mayor, a sitcom TV series with NBC, Abbott Elementary with ABC, a mockumentary about teachers in a Philadelphia public school, and Mayans MC, a drama TV series where the cast is 95% Latino. She is currently casting the biopic Weird: The Al Yankovic Story, Blockbuster, a romantic comedy with Netflix, and a new TV series American Gigolo, based on the original 1980 film.  

Freelance work and the world of film, television and casting are not for the faint of heart. Wendy comes across as very grounded, calm and balanced. How does she do it? She credits the support that she has received from her family, team members, former teachers, and lessons learned over the years, be it through sport or life experiences like those at Ridley. “Ridley taught me so much from living and co-existing with others to leadership skills, learning to compromise, and preparing me for life at college.” She went on to say, “When I think back to Ridley, I still have so many ‘aha’ moments, where the lessons taught keep resonating with me, and I am still learning from them. The Ridley teachers who most come to mind for me are Mr. Lewis and Rev. Shantz who provided subtle guidance and a moral compass. The teachers provided 24-hour support and they were visible everywhere — from the classroom and library to the dining hall, dorms and sports fixtures. I would not be who I am today without these experiences.” 

If she could give advice to today’s Ridleians, she would tell them to take full advantage of what Ridley has to offer. “Don’t wait — go for it and remember to thank your teachers before you leave.” 


This article was printed in the latest issue of Tiger magazine. Learn about our alumni, get community updates and find out where Ridley is heading next! Read more from the Spring 2022 issue.