Kyle Lowry is coming back to Canada this weekend. For 30 seconds, at least. The beloved former Toronto Raptors star is starring in a Super Bowl commercial for the Canadian crypto-marketplace Bitbuy.

Created in-house, the new “Again and Again” spot depicts an agency exec pitching a new advertising concept to Lowry. It’s built around the idea of “missed opportunities” the agency guy explains, pointing out that many Canadians still lament not buying tech stocks or real estate prior to the boom. “It’s happening again with crypto,” Lowry agrees.

The exec then shows Lowry the proposed creative, which features an image of Lowry and a voiceover pointing out that the six-time NBA All-Star and career .423 shooter has missed more than 6,000 shots during his career. “Don’t be like Kyle, and miss your opportunity again,” it says over repeated shots of a basketball clanking off a rim. “And again. And again. And again.”

“Seriously??” says a bemused Lowry before the Bitbuy logo appears, accompanied by the tagline “The crypto destination of investors.”

“We didn’t have the attitude of ‘Let’s make a funny commercial.’ It was ‘Let’s make a memorable commercial,'” said Binu Koshy, Bitbuy’s marketing and communications director.

This year’s Super Bowl has been dubbed the “Crypto Bowl”, with as many as six crypto-currency brands, including Crypto.com and the Bahamas-based FTX, all said to have purchased expensive inventory in the U.S. telecast. It’s being likened to 2000’s so-called “Dot-Com Super Bowl,” which featured ads from 14 then-nascent dot.com companies, including Pets.com and Monster.com.

Bitbuy’s ad will be the first shown coming out of the halftime show on the Canadian Super Bowl telecast, said Koshy. According to Bell audience data provided to Koshy, last year’s halftime show garnered 2 million more viewers than the first quarter average.

“I did my own research on it, and found that the halftime show out-performs the actual game,” he said. “We’re very happy with our placement.”

Until as recently as six months ago, Bitbuy’s advertising had been restricted largely to digital channels, since that’s where the majority of its users—a group Koshy describes as “early crypto-adopters”—spends much of their time consuming media.

Bitbuy has amassed 395,000 Canadian customers—with anywhere from 50,000 to 75,000 monthly active users—and boasts more than $30 million in revenue, but has reached the point where growing its customer base means attracting new customer segments, said Koshy.

“You can’t just be going after early adopters—sooner or later they’re going to tap out,” said Koshy, a longtime account executive with agencies including Grey, McCann and Segal Communications, who joined Bitbuy in October with a mission to grow its user base.

The company is expanding its marketing strategy to include more vehicles that reach Gen X and early Baby Boomers—segments for whom TV, particularly high-profile events like the Super Bowl, are still highly relevant. “Those people still live in a traditional media world,” said Koshy.

Bitbuy received registration approval from the Ontario Securities Commission as Canada’s first licensed crypto-marketplace late last year, a decision that paved the way for its advertising to be carried by major media companies such as Bell Media (which won’t accept ads from companies that are not licensed) and aligned with its strategy to broaden its audience.

Bitbuy launched its first TV commercial, “Smooth Journey,” (created with Toronto agency Elemental) early this year, but has been keeping its new partnership with Lowry under wraps since signing the deal in December.

“We naturally thought of Kyle Lowry. Even though he’s not a Canadian athlete, he’s an honorary Canadian athlete, because the Raptors are Canada’s basketball team,” said Koshy.

“The other thing about Kyle is that he’s accomplished what he needs to accomplish. It’s not like he’s an athlete in his 20s, where if he goes into a slump, he’s going to lose popularity. There’s nothing he could do where people fall out of love with him.”

And with Canadian sports fans no longer accustomed to seeing Lowry on a regular basis since his trade to the Miami Heat last year, his appearance in commercials might be enough to attract attention, he added.

Though they signed the deal with Lowry in early December, scheduling him for a shoot in time for the Super Bowl wasn’t easy.

Lowry’s only availability was a five-hour window on Dec. 22, sandwiched between a pair of Heat home games. The Toronto-based team secured a Miami-based production company and director, and shot all of the scenes that didn’t directly involve Lowry on Dec. 21 and the morning of Dec. 22.

All of this was taking place as the Omicron variant was beginning to disrupt life around the world. The NHL was already beginning to postpone games, and Bitbuy was concerned the NBA would follow suit, which would shut off its access to Lowry. “If the NBA starts cancelling games, they’re not going to allow players to go do commercials with 40 other people,” said Koshy.

Though it had nothing to do with Omicron, things did hit a slight snag when it came to casting the agency creative to star alongside Lowry. The production company put forward several candidates, but the Bitbuy team “didn’t like any of them,” said Koshy. “Five days out, we told the production company ‘We need you to see what you can find in Los Angeles.'”

They found their actor, Jared Crowe, the day before the shoot. “We saw his audition and said ‘We have to have that guy,'” said Koshy. “He had to catch a red-eye the night before the production.”

Lowry himself is actually appearing in three interconnected commercials, with the second expected to debut in time for the NBA playoffs in April, and the third tentatively scheduled for September. He will also be featured in a summer out-of-home campaign.

Lowry has appeared in ads/branded content for brands including Ford Canada, PlayStation and the water brand Nirvana Water Sciences, but tends to be selective in who he works with, said Koshy. “He was really impressed with the vision of the company and the technology.”

Lowry was reportedly also attracted by the self-deprecating approach of the ad, which was written by Koshy. “We kind of make fun of Kyle, and that adds to the [ad’s viral nature],” he said. “I wanted the video to [encourage] one of two responses: ‘That’s so funny, I need to share it,’ or ‘What did I just watch?'”

Just hearing Lowry’s name, he said, has the ability to instantly pique viewers’ interest and get them to look up from their phone during commercial breaks. It’s helped by the fact that Crowe—sounding like an unholy cross between Gilbert Gottfried and a squeaky wheel—literally screeches the player’s name to open the spot.

“Let’s say I’m watching a Raptors game or a Leafs game; it cuts to commercial, I look down at my phone to check my WhatsApp, and all of a sudden I hear [mimics Crowe’s voice], I’m going to look up,” said Koshy. “It was all intentionally done.”

Post Super Bowl, the media buy for the campaign includes various specialty channels, including TSN, Sportsnet, CBC News Network, CTV News Channel and BNN, he said.

The goal with the new advertising is to build and establish the Bitbuy brand in the small window that opens before larger global players like Crpyto.com, Binance and FTX inevitably come into the market and begin throwing around massive amounts of ad dollars.

“They’re going to come to Canada, and they’re going to have much deeper pockets than us,” said Koshy. “Because we can’t play the frequency game, we needed our spot to do the [work] of five commercials.”

The good news for Bitbuy, then, is that Lowry has shown his ability to carry a team on his back numerous times over the course of his career.