How Fate Steered Andrew Alexander Towards a Long and Successful Comedy Career

At some point in your life, you have most likely found yourself doubled over with laughter thanks to the work of Andrew Alexander, at least indirectly. As the award-winning CEO and executive producer of world-famous comedy capital The Second City, as well as the executive producer behind the legendary Emmy-winning comedy series SCTV, Alexander helped launch the meteoric careers of some of North America’s funniest people. Some of those names? Steve Carell, Stephen Colbert, Rachel Dratch, Tina Fey, Keegan-Michael Key, Tim Meadows, Bob Odenkirk, Horatio Sanz, Amy Sedaris, and Nia Vardalos.


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Andrew Alexander did not start out in life imagining that he would forge a long, successful career out of making people laugh, and he has traveled quite the interesting journey to get to where he is today.


Andrew Alexander in the Wild

Born in London, England, before immigrating to Canada as a child, Andrew Alexander attended college at Ryerson University in Toronto and Tri-State College in Indiana. After completing his education, he held jobs in several unlikely industries, including cab driver, speakeasy operator, magazine editor, waiter, and even tree salesman. As a young man still in his twenties, Alexander was seeking direction in his life and career. Five decades later, he still holds fond memories of his untethered youth and upholds that it taught him countless valuable lessons that he carried into his career in comedy.


Alexander’s relationship with The Second City began serendipitously in 1972 when he attended a show at the famed comedy theater’s Chicago home. Although he attended the show just to enjoy some edgy entertainment, Alexander found himself feeling a deeply personal connection with the art of improv and satirical comedy by the end of the night. To this day, he can still describe how that wickedly smart and rebellious experience spoke to his soul, realizing that other must feel that same visceral connection.


That night, Alexander decided to pursue a career that made people laugh, think, and maybe even see things a little differently. He wanted others to experience the same magic he felt sitting in that Chicago theater. Comedy, it seemed, was his ticket to making the world a better place and leaving a lasting impression on those whose lives he touched. At the same time, Alexander faced the harsh reality that making it in the comedy world is not easy, and even the most thick-skinned need to prepare themselves to face relentless rejection.


How Andrew Alexander Built His Career as a Comedy Producer

Armed with a new sense of direction and purpose in life, Alexander approached the co-founder of The Second City, Bernie Sahlins, with an irresistible offer. Backed by a loan from a friend, he took the helm of the Toronto branch’s failing location and breathed new life into the struggling comedy club. With a passion for the art and a creative mind for business, Alexander’s revamped theater soon had audiences coming in droves to watch then-unknown superstars like Catherine O’Hara, Eugene Levy, and John Candy in action.


From the Stage to Television: SCTV

In 1975, NBC launched an experimental sketch comedy show that the world knows today as Saturday Night Live. The first cast included Second City talent Gilda Radner, Bill Murray, and Dan Aykroyd. Alexander’s desire to launch an original television show was driven just as much by an attempt to hold on to his talent as it was to create the raucous, unforgettable world of SCTV. The groundbreaking show premiered on Canadian television in 1976 and went on to earn millions of fans around the world. During its six seasons, the comedy show earned two Emmy Awards and made household names out of talent like Martin Short, Rick Moranis, and Andrea Martin. Alexander remains endlessly proud of the offbeat characters and wild parodies SCTV created on a shoestring budget, a production that was born very much out of The Second City’s “DIY” DNA.


Taking Charge in Chicago

After turning around a once-shaky Toronto theater and producing one of television’s most iconic comedy series, Andrew Alexander set his sights back on Chicago. In 1985, he and his business partner Len Stuart purchased the remaining interest in The Second City, marking its first ownership change since being established in 1959. The new beginning sparked a rapid expansion in the comedy theater’s footprint. The founding of The Second City Training Center created a formal education program for aspiring comedians, and today, the institution has grown to become the world’s largest school of improv and comedy arts.


Alexander’s efforts helped establish Chicago as an international hub for nurturing and developing exciting new voices in comedy at The Second City. Not only were the theater’s shows sold out months in advance, but those who wanted to one day make it to a world stage knew that their best bet was to come to Chicago and The Second City to train.

Hollywood and TV networks took notice, and Alexander’s stature in the industry quickly expanded to include a slew of projects for major networks. The world was hungry to laugh, and Alexander was happy to serve up incredible talent and material.


“Failing Up” While Building a Career in Comedy

After almost fifty years in the comedy world, Alexander has plenty of advice for new performers. One of the most important things up-and-comers should remember is that no one starts at the top. People who are revered as great comedians today began on much smaller platforms. In fact, one of The Second City’s most important principles is that its cast members are not a group of individuals trying to make it big. Rather, they are a true ensemble who fundamentally understand that the best way to make themselves look good is to make their peers look good on stage. That has been the key to finding success at The Second City…and beyond.


According to Alexander, learning to build resilience and not allowing the opinion of one person–or even an entire audience–cloud how they seem themselves as performers is not only freeing, it’s necessary. “Failing up” is an expression any newbie should learn to embrace, because learning from feedback is not only inevitable, it’s invaluable.


Patience is also important, as Andrew Alexander demonstrates with his own career. The one-time hotel management student who has worked with everyone from former Canadian First Lady Margaret Trudeau to Martin Scorsese describes trusting his instincts to know when the time was right to move on to new opportunities and recommends that other comedians also take this approach.


Pursuits Outside of Comedy

Although Andrew Alexander is proud of how his work has influenced and shaped the comedy industry, his desire to leave a lasting impact reaches beyond the stage and screen. He appreciates the opportunity to work with a variety of organizations that better the lives of artists behind the scenes. One of Alexander’s proudest achievements is the creation of The Second City Alumni Fund, founded to support members of the comedy community experiencing critical health and financial challenges.


At a time when people need joy more than ever, the ripples created by Andrew Alexander in the comedy world continue to bring thought-provoking humor to generations of fans. At 76 years old, he is still going strong, eager to again set his sights on an unknown, uncharted, and laughter-filled future.