Nothing, till now, makes Jack Armstrong nervous. Not speaking to a room with hundreds of people – he’ll jot a few words on an index card, probably not even glance at it again, and riff for an hour.
Not looking into a camera lens and going live on television. “When the red light comes on and they say, ‘Oh, by the way, it’s a big game tonight, we’ll probably have a million people watching,’ that doesn’t bother me,” says Armstrong, a Lewiston resident and former Niagara University basketball coach who works in Toronto as a broadcaster for the NBA’s Raptors.
Not performing, either. A Brooklyn native who has never lost his New York accent, Armstrong has embraced elongated vowels and R’s that become “aahhs” and developed signature lines that are famous among Canadian basketball fans: “Hellooooo!” (or sometimes the French “Bonjouuur!”) for a big play, and “Get that gah-bage outta here!” for a blocked shot.
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“I’ve never really seen him nervous about anything, except for the day we got married,” says Dena Armstrong, his wife of almost 30 years.
Armstrong is chatty and effervescent, a natural showman and extrovert to the extreme. “We could be in line at the supermarket,” Dena says, “and if somebody wants to talk to him, he will talk.”
He’ll sing, too, in many settings: a family party, a bar, even on TV.
But singing in an actual concert hall? That was something different – and something he was about to do for hundreds of people filling the seats inside Toronto’s Danforth Music Hall on a Tuesday evening in early December. It was something he hadn’t planned on happening when he agreed to do this funny music project, and something that was now making him feel a sensation that is unfamiliar to him.
“It probably didn’t look like I did,” Armstrong says, “but I had a knot in my stomach the whole time.”
Jack Armstrong, coach-turned-broadcaster-turned-recording star, was finally feeling nerves.
When Armstrong was approached a couple years ago by a Canadian entertainment entrepreneur about recording a Christmas album, it wasn’t too hard for him to say yes. The son of Irish immigrants, Armstrong has long loved to break into “Danny Boy” at a bar or a party, or sing Christmas carols on air, which is what caught the attention of Barry Taylor, the managing partner of Toronto-based Comedy Records.
“One night I was sitting on my couch watching the game and he was singing along during the broadcast,” says Taylor, a comic who had met Armstrong a couple of times at TV appearances and had the broadcaster’s business card. “I had one of those ‘aha’ moments.”
Taylor told his Comedy Records partner, Tim Golden, “I’m going to reach out to Jack about doing a holiday album.”
Taylor made the pitch to Armstrong, whose first reaction was, “You’re nuts.”
But Armstrong’s entire broadcast career is one that happened because he keeps open possibilities and embraces the power of a well-placed “yes” – or, at least, a “why not?”
Armstrong became a broadcaster after a decade of coaching at Niagara, one that began with him being the country’s youngest Division I men’s basketball coach (he was 26) and ended in 1998 with a disappointing 100-154 record. He interviewed to join the then-relatively new Raptors franchise as a broadcaster, recruited a team of highly placed basketball friends to help him lobby for it, and landed the job.
Armstrong’s abilities as a talker, on-camera performer and teacher of the game made him a star across Canada. He embraced his growing fame, but not with a sense of self-importance. Armstrong didn’t, for example, launch himself into social media, the growth of which over the last two decades roughly coincides with his own rising fame. (He has a Twitter account for marketing purposes, but doesn’t personally run it.) “He’s a total rock star over there,” Dena says. “In his mind, he doesn’t quite see it that way. We can all see that, but he doesn’t actually think that.”
Armstrong’s acceptance of his fame is marked by a sense of openness. When some Canadian entrepreneurs approached him about creating a line of merchandise with his famous sayings, he said yes. (That’s also when he finally agreed to open a Twitter account to promote it.) Likewise, when Armstrong heard the hard pitch from Comedy Records – “They’re like, ‘We think it would go well. … We could have an album, we could do a concert …’” – he also said yes.
Getting the project into a recording studio took some time: Armstrong wanted to wait until Covid-19 was under control and Canada’s pandemic restrictions were reduced or gone. “I wanted to do this at a time when people were back in the mood to celebrate the holidays as more joyous,” Armstrong says.
Last spring, Armstrong spent a couple of days in a Toronto rehearsal studio working through a variety of Christmas songs, ultimately settling on 14 for the album, which was recorded with the Comedy Records Band (five instrumentalists, two background vocalists) after the Raptors’ season ended. “Hellooo & Happy Holidays from Jack Armstrong” dropped in November on music streaming platforms and on vinyl. The album artwork features an illustration of Armstrong, who is tall and lanky and conveniently sports a fuzzy white (albeit trim) beard, in a Santa hat on the cover and steering a sleigh on the back.
The tracks include several Christmas classics that Armstrong sings straight, plus some with a couple of twists that are easily understood by anyone who knows Armstrong as a basketball broadcaster with signature lines: He plunks a high-pitched “Hellooo!” into “Holly Jolly Christmas” and recites a basketball-themed version of “T’was the Night Before Christmas:”
T’was the night before Christmas
Not a creature was stirring
If you’re wondering whether Armstrong can actually sing, the answer is a straight yes: He can carry a tune. At 59, a future recording star he is not. But when Taylor and Golden saw him in rehearsals, they were surprised at Armstrong’s ability to deftly sing an array of Christmas songs. “We were like, ‘Oh, wow, this is something that can be much more than we’d originally planned,’” Taylor said.
That seeded the idea of having Armstrong headline his own show— a notion that, even for a guy who seems endlessly curious and creatively fearless was finally, undeniably, someone that would make him nervous.
On the first Tuesday night of December inside Danforth Music Hall, the stakes were relatively low.
Tuesdays are a calm night socially; they tend not to be loaded with parties and shows and, thus, choosing to see Jack Armstrong sing probably didn’t mean you were skipping another concert by, say, a more seasoned performer.
Christmas music is crowd-friendly. People know it, like it, and can help you sing it. For Armstrong’s show, which was advertised as a singalong, a huge screen behind the stage flashed the lyrics he was singing, an unsubtle way of reminding the crowd that they, too, were part of this show.
None of this was for Armstrong’s profit, either. The show, and album, benefit the Maple Leaf Sports and Entertainment Foundation and Special Olympics Canada.
Plus, to be real about it, Armstrong is a giant and beloved pop-culture figure in Canada; he wasn’t going to lose fans if he lost his melody onstage.
“I was nervous about it, and anxious,” Armstrong says, but then injects an oft-used coaching line: “I felt good because we were prepared.”
Armstrong and the band had three rehearsals in the weeks leading up to the concert, and as a safety measure to be sure he didn’t forget any words, a monitor was set up on stage to scroll the lyrics. (This is a relatively common practice even for top-level musicians.)
Dena, who was staying in the Armstrongs’ Florida home, flew back north for the show with the couple’s eldest son, Kevin, and Kevin’s fiancee, Alyssa. Dena arranged for a busload of about 40 Western New Yorkers to be part of the audience, which was otherwise filled mostly with people connected with the Raptors, the charities involved, and basketball fans.
Before the show, the Western New York crew gathered at a bar near the venue. Armstrong stopped in briefly to say hello, but declined to have a drink. “I have to be on top of my game – I can’t,” he said.
Dena, noting her husband was “a bit apprehensive, nervous a little, which I’ve never seen,” asked Jack if he was feeling nerves.
“A little bit,” he admitted.
But the tension would melt away. Once the show began and Armstrong got through the first couple of songs, “he overcame the whole thing,” Dena recalls.
The same Jack Armstrong who has charmed Canadian basketball fans for a quarter-century – his wide-faced smile, his lanky frame clad in a suit as he points expressively – emerged. He revved up the crowd into singing along and then, as performers are wont to do, took them on an emotional journey. In the middle of the show, Armstrong broke briefly from Christmas to speak about his mother, Mary, who is 95 and still lives in New York. She emigrated to the United States with his father, who died when Jack was 7, and raised her sons as a single parent. Armstrong had a pint of Guinness and a shot of Jameson Irish Whiskey delivered to the stage. Finally open to having a drink, he indulged in those Irish beverages and sang an a cappella version of “Danny Boy” for his mother.
Then he turned to Dena. Armstrong spoke about their decision to adopt three boys, and her dedication in raising them while he was gone so often for basketball through the late fall, winter and spring.
Dena, sitting in the crowd, was already feeling emotional. “When he first came out and started singing, it brought a tear to my eye because I’m like, ‘Oh my God, he’s actually pulling this off,’” Dena says.
The emotions built as Jack began talking about his mother, and then about Dena – which she wasn’t expecting. “To understand how much he actually cares about me, I mean, I get that, I understand that,” she says. “But to hear him actually tell the world, it’s a whole different experience for me.”
Basketball broadcasters can’t typically get that personal. But singers can, and on this night, that Toronto stage belonged to Armstrong. After speaking of Dena and before turning back to the Christmas songs, he told the crowd he wanted to sing his favorite-ever song, one written by a Canadian-born music legend – Paul Anka, of Ottawa – for an American icon from Hoboken, N.J.
Armstrong looked into the crowd and began to sing “My Way.”
Frank Sinatra, he is not. But Armstrong still took the stage and did it his way.
When the broadcaster for the NBA Champion Toronto Raptors finds a microphone, he knows how to use
Jack Armstrong wasn’t sure if he could easily bring the NBA’s championship trophy over the border from Canada into the United States. He knew it wasn’t illegal, but the Larry O’Brien Championship Trophy is 2 feet tall, shaped like a basketball falling into a net, and plated in gold. It’s not inconspicuous. But Armstrong had to get the trophy
In Lewiston he’s just Jack, but in Canada, where he has worked for 18 years as a broadcast analyst for the Toronto Raptors, Jack Armstrong is a national