Growing up, I never thought about advertising or marketing.
Sure, some commercials caught my eye, but the ins and outs of what happened behind the scenes didn’t tickle my fancy.
I was far more interested in history… and still am… which is why I’m so happy I got to speak to today’s guest.
He has helped me discover the fascinating world of advertising. From the stories behind my favourite commercials, to what makes brands succeed.
I’m Craig Baird and this is Canadian History Ehx … Biography!
For years I’ve been listening to today’s guest as he helped us all understand the world of advertising a bit better.
This is…Terry O’Reilly!
Every morning as a child, I sat down in front of the TV to watch my favourite shows.
Mr. Dressup.
The Friendly Giant.
And Romper Room.
Every morning, I waited for the end of Romper Room, when the host would look into a magic mirror, and straight into the camera.
I would hold my breath as she named all the people she could see, and I waited for her to say those magic words…
“And I see Craig!”
But she never did.
Not that I’m bitter about it or anything.
I may have been hoping for a name drop, but Terry O’Reilly got so much more than that.
He was on the show.
Terry O’Reilly had been born on July 7, 1959, in Sudbury, Ontario and by the time he was four he was appearing on the Canadian version of Romper Room.
The children’s series targeted preschoolers and featured a hostess and a group of children embarking on games, exercises, songs, story-telling and moral lessons all accompanied by music.
While he was appearing on Romper Room in the early-1960s, he was asked to star in a TV commercial for a local bakery. While he was on the set, Terry ad-libbed a line that made the director laugh.
And with it… A star was born!
From then on, his path was clear.
He was going to entertain even if it took him a few years to figure out how.
Thankfully he got a leg up in high school because he was fortunate enough to have a full television studio at his disposal.
Terry O’Reilly says it helped him hone his
Terry had his eye on Ryerson, now Metropolitan University in Toronto for his post secondary education.
He says the program he was interested in was in high demand and that studio gave him a massive leg up during the application process.
The reel helped him get accepted into the radio and television program.
It continues to be one of the best programs in the country and when Terry was a student every Wednesday the university would invite someone from the industry to speak to students.
One week it could be Lloyd Robertson, one of the most famous journalists in Canadian history, another week it could someone else… like Canadian icon Bob Homme, better known as The Friendly Giant, from the popular children’s TV show that aired on CBC for decades until the 80s
On another occasion the school invited advertising industry experts.
Terry sat and listened intently as they shared what they did for a living.
He says that what he heard sparked something in him.
He would now be on the path towards advertising and once he graduated he began his first pitch.
Himself. With high hopes, he sent out 60 resumes to 60 advertising agencies and received 60 rejections.
(PAUSE MUSIC TRANSITION)
Terry O’Reilly was determined, no matter how many rejection letters he received, he didn’t give up and eventually landed a job as a copywriter.
He never looked back.
Soon people noticed that not only was Terry a great writer…he could also make people laugh.
A skill he had since he was a kid on set for the local bakery commercial
And making people laugh is a great way to sell products.
Before long, O’Reilly was on national campaigns working with some of the most famous Canadians in the world, while traveling the country and doing what he loved.
And as the saying goes if you love what you do you will never work a day in your life.
So eventually Terry felt he needed a new challenge and a new way to spread his wings so to speak.
Terry O’Reilly co-founded Pirate Radio and Television in 1990.
It would be an audio production company that produced scripts, sound and music for radio and television commercials.
What started as a small operation has grown to include 50 staff and eight recording studios in Toronto and New York City.
With Pirate Radio and Television, advertising agencies were now his customers, and Terry wouldn’t just be writing commercials, he would be directing them as well.
He says his unique set of skills made his new company sought after by agencies hoping to make customers laugh.
His strength had only one weakness when Terry discovered that Canadians and Americans find different things funny.
Canadians are heavily influenced by British humour, which tends to be dry and more surreal. They’re also humbler than their southern neighbour and love of self-depreciation.
Managing the differences in American and Canadian preferences was one thing, and to a certain degree it makes sense, they’re different countries.
But Canada’s size became another challenge. National campaigns had to appeal to people in British Columbia, but also in Newfoundland and everywhere in-between.
As anyone who has traveled across Canada can attest, people can be very different from one province to the next.
Terry says this is why he focused on more than demographics when he looked to create his ads.
You never know what is going to click with Canadians either.
Long before Moo Deng stole hearts on the internet and became a sensations Canadians fell in love with a tiny hippo who lived in their homes thanks to a PSA about false advertising.
I mean, I’m literally wearing a House Hippo hoodie as I write this.
In the 90s The I Am Canadian campaign by Molson as a pitch seemed likely to resonate with Canadians, but it wasn’t a sure thing.
Turns out it did and this year we got an updated rant from Joe Canada as Canadian nationalism surged.
But in advertising figuring out what is going to click with customers is uncertain.
A lot of factors are needed for an ad to become part of culture.
And sometimes a commercial you think is going to flop, ends up far exceeding expectations.
Terry says knowing what a hit will be is in the end a bit of a mystery.
Terry has experienced this firsthand when he was working with a French wine brand.
His agency had created an ad that mirrored a classic French film with subtitles.
Unfortunately, the client didn’t like the commercial and tore through the script.
Terry truly believed they had a disaster in their hands.
Even though he had never been to the City of Love, he was so angry he refused travel to Paris, to film the ad He says he was surprised by what happened when the ad came on the TV.
By the mid-1990s, Terry O’Reilly had spent roughly twenty years in advertising.
He was directing upwards of 500 commercials a year and knew the industry inside and out.
And that… gave him an idea and a place where he could stretch too next.
Terry O’Reilly was sought after as a creative and soon he would be one of Canada’s best teachers.
In the mid 90s at what seemed like the peak of his career he rented out a Toronto theatre to share his knowledge.
He invited 200 young copywriters from across the country, provided them with breakfast, lunch and an open bar, and for seven hours and taught them everything he knew about radio.
Terry shared his secret for script structure, the difference between writing 30 seconds versus 60 seconds ads, studio protocol, how to work with a music composer and how to manage talent.
The seminars were always popular, and he says that one day while having a drink with friends, an idea was hatched.
He initially laughed off the idea, but then he couldn’t get it out of his mind.
Mike Tennant, who was also a veteran of print and radio writing, was also at that lunch.
He also couldn’t shake the idea away and he called up Terry to develop a pitch.
Terry y didn’t think anyone would buy it, he said he went with Tennant and the two met with Chris Boyce, who was then the head of CBC Radio, and gave him a 30 second pitch.
Boyce was wowed and ordered the show for the network.
Now, O’Reilly and Tennant had to make it happen.
The show became On Advertising, and it premiered on CBC Radio in 2005.
A year later, it became Age of Persuasion, a hit series which was lively, entertaining, and packed with advertising stories and practical examples.
It ran for five years and during this time is when I was first introduced to Terry O’Reilly and became a fan of his work.
I wasn’t the only one.
The show received critical acclaim for its informative and humorous take on advertising.
Terry suddenly had fans across the country.
He went from behind the scenes to the spotlight and in the process helped helping Canadians navigate the world of advertising.
By 2011, Mike Tennant had left to work on other projects, and Terry realized the world had changed drastically.
In that time the world of podcasting had emerged Terry saw the potential to reach new audiences who didn’t listen to terrestrial radio.
He said listeners could now listen to his show any time.
When he first started Age of Persuasion, social media wasn’t what it is today.
Facebook and YouTube were only a year old, and Twitter, Instagram and TikTok didn’t even exist.
But in only five years, O’Reilly saw the industry had gone from hardcore persuasion to one ruled by algorithms.
He said the changing landscape helped him reinvent the
That gave birth to Under the Influence.
It debuted in 2011 and quickly earned similar acclaim to his previous show.
It was named the Best New Podcast of 2011 by Apple Podcasts, and Best Radio Program by the New York Radio Festival in 2011 and 2012.
In the early days, podcasting was considered fringe media but today it is at the forefront and growing in popularity by the second.
But for as much as Under the Influence continues to delight listeners each week, Terry says that the biggest challenge for podcasting continues to be discoverability.
This is something I know well as well because for as much as Pierre Berton inspired me in history, Terry O’Reilly inspired me in podcasting.
And I try to take the same care with my show, as he does with his.
When I choose a topic, I select something that my listeners will find interesting. It’s not just something I want to talk about but what my audience wants to listen to as well.
Terry says that for him it is about finding that balance.
The world of advertising has changed immensely since Terry first hits the airwaves.
Before the Internet, advertisers had a one-way conversation with audiences.
If someone wanted to complain or give feedback, they needed to write a letter, find a stamp, go to the post office, and mail it.
It was a lot of effort, and they likely never hear back from the company.
Terry says all of that has changed.
Everything has also become more fragmented. Gone are what used to be called water cooler moments.
Terry says grabbing eyeballs isn’t as easy as putting up a billboard, or buying up television, radio and newspapers, ads.
Every year it seems there’s something to give Terry plenty of content to talk about.
Right now, we are dealing with a wave of nationalism, and that is changing how Canadian companies are advertising to consumers.
People have rallied around Buy Canadian while American products sit on the shelves,
Terry sees this as a positive trend.
When O’Reilly was a young boy, the Golden Age of Advertising was in full force. The era of Mad Men, when boundaries and rules were constantly broken and reinvented.
So where does the advertising world go from here?
Even though advertisers and directors have a lot of choice, Terry fears other challenge.
If we do reach that second age for advertising, there is no better person to guide us through it than Terry O’Reilly.
He has been honoured with Lifetime Achievement Awards from three different industry organizations, and he is a member of Canada’s Marketing, Advertising, PR and Communications Hall of Fame.
He also has three honorary degrees.
Not too bad for a career that started with an ad-libbed line in a Sudbury bakery commercial.
I would like to thank Terry O’Reilly for sharing his time with me. In two weeks, we will be back with another episode of Canadian History Ehx Biography.
I will be talking to singer-songwriter Ron Sexsmith!
