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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.

Celebrating the Arts at Ridley

The arts play an integral role in leading a flourishing life. The opportunity to explore creativity and practice self-expression allows Ridleians to define who they are, gain confidence in their talents, unlock the potential to innovate and contribute to culture. Great importance is placed on this aspect of student development at Ridley. Students are given the opportunity to create in any way they see fit. Ridley offers both academic and extracurricular options to explore music, drama, visual arts, digital arts, design or the spoken word. Students enrolled in the International Baccalaureate programme have a creativity element integrated into their curriculum as well.

In support of this approach, Ridley recently hosted Arts in April. This series of events captured all aspect of arts on campus. Members of the Ridley community were encouraged to attend and engage with our talented musicians, performers, artists and film makers.

Visual Art Showcase

Arts in April began with a visual art exhibition at Brock University’s Rodman Hall. The Visual Art Showcase allowed our Grades 7 to 11 students to display their artistic works in a public art gallery. The exhibition held its opening night on April 6th, with Headmaster, Ed Kidd sharing his excitement for the partnership between Brock University and Ridley. For the remainder of the evening, members of the community, Brock and Ridley perused the collection, speaking with the artists and admiring the wonderful works on display. The exhibition was open to the public until April 16th.

View photos.

IB Graduate Art Exhibition

“The IB art exhibition was an unforgettable experience; I was not only able to present and reflect on my works as an artist, but also suspend my belief and dissect them as a viewer.” – Monika Morcous ’17

From April 18th to 20th, the Griffith Gym was home to a large collection of art created by IB Art students. All senior IB student were given a section of the gallery where they could display several of their pieces. The works of art on display for the IB Graduate Art Exhibition were taken from a series of studio works undertaken over the two year IB Visual Art course. These works make up the exhibition component of the course, in which each student is required to generate series of artworks that reflected a specific theme and evidence of mastery using a chosen medium. Students enrolled in the SL (Standard Level) course were required to complete seven works of art and students enrolled in the HL (Higher Level) course needed to complete 11. In addition to the exhibition component of the course, students were required to complete a process portfolio and a comparative study paper. Each display was unique, allowing a glimpse into the artists’ creative process, style and technique. The sheer talent, creativity and focus of our IB Art students was impressive.

View photos.

Ridley Independent Film Festival

On April 19th, a red carpet was rolled out in the Mandeville Theatre for the 9th annual Ridley Independent Film Festival, better known as RIFF. This film festival is entirely student-run and was an opportunity to showcase the creative works of the IB Film Studies students.  Each student group was tasked with creating their own short film, from conception to execution. As each film premiered, it was clear that each student involved – videographer, producer, editor, actor or otherwise – was committed to creating a top-quality short film. For several students, this was the perfect opportunity to build a portfolio and get first-hand experience.

View RIFF films.
View photos from the red carpet.

Celebration of the Arts

On April 25th, the Upper School gathered together for the annual Celebration of the Arts. The event began in the Mandeville Theatre, where Head of Upper School, Michele Bett, inspired students with the trying stories of artists, musicians and performers from throughout the ages.

“Rationality, or thinking with the head, is one half of our human inheritance; the other half is creativity, or thinking with the heart. And I submit that this is the place of the arts, both at Ridley College and in our culture as a whole. The place of the arts is the heart.” – Michele Bett

To follow, students from the Music, Performing Arts and Digital Arts programmes performed pieces for their peers in the audience. Our string musicians played a spectacular piece from Star Wars, followed by a song from Hamilton, the musical. Raylon Chan ’19 rapped alongside them and brought the audience to their feet for a standing ovation. A number of IB students showcased their studies during a theatrical piece that told a story through movement. The Jazz Band also performed on stage, after a playfully animated video on the negative effects of climate change. When the spectacular display of performing arts concluded, students reconvened in the Griffith Gym for a visual art exhibition, showcasing the works of both Upper School and Lower School students.

Read Mrs. Bett’s full speech.
View photos.

Upper School Art Awards

To conclude Arts in April, students from Grades 9 to 12 joined in the Mandeville Theatre one last time for the Upper School Art Awards on April 26th. This award ceremony is an opportunity for our students to celebrate the accomplishments and achievements of their peers. Interspersed throughout the award presentations were musical and theatrical performances. Faculty members from the Department of Music: Scott Vernon, Clyde Dawson and Ken Hutton joined Anthony Nguyen ’18 on stage for a fantastic musical performance to begin the night. Dramatic Arts students performed scenes from Ridley’s production of The Tempest.  The String Orchestra, Cadet Band and Senior Choir all performed on stage – sharing both classical and modern songs. Finally, audience members were treated solo performances from Petrina Mo ’17, Alessia Guarducci ’18 and Jim Li ’17. To conclude the event, Senior students, Petrina Mo ’17 and Padraic Odesse ’17 spoke of the importance of the arts at Ridley; not only as a means for self-expression, creativity and culture, but also as an opportunity to expand one’s horizons and make connections.

View photos.

While Arts in April may be over, Ridley’s dedication to the arts continue. In May, our youngest Ridleians are showcasing their creative works at the PYP Visual Arts Showcase, followed by a musical performance by the entire Lower School student body.

Tigers Meet in Times Square 

On November 10th – 14th, 2016, two groups of Ridley students journeyed to New York City, where they would spend their weekend exploring the many different facets of the Big Apple. For 40 students, the trip was purely about taking in sights and sceneries, while another group of 30 Tigers set out to be artistically inspired. What was not on the itinerary was a serendipitous meeting in Times Square.

Our larger group of students represented Ridley well, as they wound their way through the many “musts” of New York. The students visited the Brooklyn Bridge, experience Fifth Avenue and strolled through Central Park – where they partook in the viral sensation known as the Mannequin Challenge. Some students also visited the new World Trade Centre site and Strawberry Fields.

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The other group – comprised of Grade 12 Visual Arts, Design Technology and Film students – hopped from one gallery to the next, as they explored the world of creation throughout the ages. Their stops included the Museum of Modern Art, the Cooper Hewitt Design Museum and even the Cathedral of St. John the Divine, where they could appreciate traditional and modern masonry. While the focus of this group’s trip was to discover and explore creative expression, they too made time to visit some of New York City’s highlights, such as Times Square.

As the weekend progressed, both groups made time to visit one of the world’s busiest pedestrian intersections, preparing themselves for the overwhelming experience that is Times Square. What they weren’t prepared for was running into their friends from home. Completely unplanned, both Ridley groups managed to find one another amongst the hustle and bustle of Midtown. It was a serendipitous moment that led one to feel that no matter where you may find yourself, a fellow Ridleian is never far away.

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On Monday, the students made their way back to campus, with many stories to tell their friends and families.

The weekend was an awe-inspiring one for all who were present. Each Tiger was able to explore the big city and discover something that spoke to them – be it a piece of history, a piece of art, or a piece of pizza.