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From Brooklyn to Toronto: How two Raptors broadcasters joined the ranks of Crosby, Ives and Carey

Last year, Sean Woodley did an oral history of Jack Armstrong and Eric Smith’s infamous holiday album recorded in December 2010. The site he wrote if for has since been wiped from the internet, so we’re giving it a new home on the eighth anniversary of the infamous recording session.

NOTE: This piece was written for last year, but that site has since been wiped from the internet. We’re making HQ its new home, though a couple slight edits have been made to make it more up to date.

On a blustery December night in 2010, a work of art was recorded in a Toronto radio studio. Sgt. Pepper’s Lonely Hearts Club Band, The Velvet Underground & Nico, My Beautiful Dark Twisted Fantasy — those perfect assemblies of songs that work of art is not. No, From Brooklyn to Toronto: Jack Armstrong and Eric Smith Sing the Holiday Classics, the musical debut of two long-time Toronto Raptors broadcasters, is something else entirely.

From the perspectives of an ex-coach with rasped-but-soulful vocal chords, an amusia-addled radio play-by-play man, a pianist thrust into an unexpected spotlight, and a jilted broadcaster left out of the creative process entirely, this is the story of how a handful of playful on-screen verses turned into the 27-minute festive ride that can only be described as: “so bad it’s good.”

The Genesis

In the years that preceded the album’s recording, Jack Armstrong had become known for his propensity for bursting out into song during Raptors broadcasts. Those random flourishes peaked around the holidays, though the song choices were not restricted to Christmas tunes. Somewhere out of the thicket of Armstrong performances arose an idea.

Eric Smith (Raptors TV Sideline Reporter & Radio Play-by-Play Announcer, Sportsnet): During the Christmas season, he sings Christmas songs all the time. Dan Gladman, the producer on the TV side, we’ll often, even if Jack’s not even around, I’ll just pass Dan on the plane and I’ll just go like “happy holidayyyys,” and that’s all. That’s the only line.

Jack Armstrong (Raptors TV & Radio Colour Analyst, TSN): I’ve spent a lot of time in bars… so I think you learn to sing in front of jukeboxes. I love singin’ Sinatra songs, and I love singin’ Chistmas songs.

Matt Devlin (Raptors TV Play-by-Play Announcer): You know how it started, I wanna say we were in Detroit, and I believe that in a commercial break, the arena was playing Bon Jovi — Livin’ on a Prayer –and we were singing along with it for fun. And we came back from a break, and I think just for fun the guys in the truck rolled it back so you could see us and hear us kinda singing along.

Here is the video Devlin’s referencing. They are more than “kinda singing along.” Note the posting date: December 11th, 2010 — just five days before the estimated recording date of ‘From Brooklyn to Toronto,’ Thursday, December 16th.

Devlin: And then at the holidays — I wanna say, more than likely, at that time, Jack was already on the air singing some Christmas songs and carols, and I think that’s kind of what then put the album in play, or why they were like “hey let’s do this.”

Armstrong: Eric and I were doing a radio show together on The Fan 590 if I’m not mistaken.

Smith: Yeah I think it was that… ’cause we were on for about 20 months or so, just shy of two years total so I think it was right in the middle of that. We used to joke about doing one show every once in a while where we would do karaoke bumpers instead of just regular bumper music. Of course being on the road — I sing sometimes, Jack sings all the time — but the odd time if we would find a karaoke bar we would end up invariably, at some point singing karaoke, where I might do a song or two, Jack would do about ten.

Interviewer: What’s your go-to karaoke song?

Smith: David Lee Roth – Just a Gigalo. And Jack’s heard it. When I get to the “Humala bebuhla zeebuhla boobuhla” it’s a real crowd-pleaser.

Devlin: [Jack] loves to sing Frank Sinatra. He absolutely loves it. I used to have an entire file full of video of Jack singing and I actually had to delete it all just because I didn’t have enough storage left on my phone. (Why Matt did not email it to somebody before deleting it is unclear, and a tragedy.)

Look, he loves singing and it doesn’t even take a karaoke mic for him to get going.

Armstrong: And we had a lot of fans, cause I used to sing all the time, and I still do on the air. And then we were doing the radio show at The Fan, I would sing a lot of times on the air just as a joke, and people kinda requested “why don’t you do something!?”

Smith: And then it just sorta sprung from there. I said “Jack, we should do this for like a charity thing and actually make an album.” I think that’s kinda how it started.”

The Search for Help

While Jack — and to a lesser extent, Eric — had the singing thing down, the album never would have become reality without someone with legitimate musical acumen. Eric began a search around The Fan’s headquarters.

Josh Gold-Smith (Former Producer, The Fan 590 / Pianist): There’s a guy at The Fan named Jaspreet Mangat — he’s the heartbeat of the station, he’s the head audio and web editor in the office, and he knows everybody. I believe Eric called him one day and said, “Hey Jas, do you know anyone who plays piano at the station cause we need a musician to accompany us.” And Jas just happened to know that I played — I had already been there as I said for a few years, and maybe in the course of our conversations it came up… I was playing in a band at the time or not too long before that.

Eric knew me because I’d worked with him on Raptors broadcasts previously… And then randomly one day I just get a phone call, it was I think early December, I just get a random phone call from Eric Smith… I didn’t get too many calls from Eric, I didn’t know what it could possibly be about… If he was calling me it must have been something big.

Smith (via e-mail clarification): There wasn’t much to it. He (Josh) was a producer / part time jack of all trades (from what I recall) at the station at that time. But either way he was more than willing to help out and put in the time. He was the real (only?) musical talent on in the album!

Gold-Smith: It was just really out of left field… And I said “yeah I play! Christmas music isn’t exactly my thing but it sounds like a fun project and I’d be happy to help you guys out.” So I said “when are you guys recording?”

Smith (as told by Gold-Smith): Tomorrow night.

Gold-Smith: I sorta went “oh boy.” So now I have to learn all these songs in whatever it was a 24 hour, 48 hour turnaround. I just basically went home and printed off a bunch of sheet music and tried to learn as many Christmas songs as I could in a few hours… over the next day or two I kinda solidified a few tunes, and then we went in to record.

And the recording of it is a whole other story…

The Session

With Gold-Smith’s talents secured, recording proceeded on a Thursday — December 16th, 2010. In a tucked away studio at The Fan 590 — definitely not the ones you see on TV, per Gold-Smith — the recording session began. Time was not on the trio’s side; there wasn’t even a moment or two available for any kind of festive mood-setting.

Gold-Smith: There was no dim lighting. No Christmas lights or mistletoe or anything like that, that I can remember for a fact. I think they were just wearing their normal radio show attire cause I think the show was simulcast. I don’t think [Jack] was festively dressed… it was very low key for Christmas Jack, if you will.

We were all in the same room, Jack and Eric had their own microphones… I actually brought my keyboard to the studio, I threw it in a cab, and cabbed it over to the studio and I brought it up cause I wanted my own thing that I used… We set up, I had my own kind of space and my own microphone and everything. I wasn’t planning on doing any singing. And the two guys had their own mics — they might have been hand held, the kind you can pull off the stand and walk around with. I do remember them kind of standing up as they were doing it.

Armstrong: We did a Hoops show on a Thursday night [Armstrong and Smith’s weekly show], and we [recorded] [the album] before the Hoops show.

Gold-Smith: The plan was, they were gonna record it before they recorded Hoops. They figured no problem, we’ll get there a bit early.

Smith: I think we originally wanted to do it between like 4 and 6 and give ourselves a good window and give ourselves the opportunity to do multiple takes and edits, cause we knew we would need it. And for whatever reason — I can’t remember if it was Josh, if it was set-up, if it was our schedules, whatever the hell it was — it was 6 o’clock or just close to six before we started and we’re like well, “We gotta get on the air at seven o’clock, it’s live so we have no option,” so we banged it out.

Gold-Smith: In theory that was a brilliant idea. In practice…

The turnaround for me already was a little crazy… And then they said “OK we gotta get this done around 7 o’clock” and I’m pretty sure we started around 6 or something like that. We somehow cranked out this 14 song set-list, plus the spoken word part [The Night Before Christmas] in about an hour or less. It was a real bang-bang thing.

Armstrong: I can’t remember the songs we sang at this point. I remember there was a guy with an organ in the background… it was so cheesy.

Gold-Smith: They were kind of taking my lead… They’d say alright let’s do the next one, and I’d just sort of launch into it and they’d sorta follow…

Smith: And I remember a couple times we’re telling Josh like “Come on Man! You gotta keep up let’s go!” Meanwhile he’s the one that actually knows what he’s doing and we’re like “PICK UP THE TEMPO JOSH LET’S GO!”

Aside from a couple verses on ditties like ‘Silver Bells’ or ‘Deck the Halls’ (on which Paul Jones was featured), none of Jack or Eric’s performances would be classified as “good.” But ‘Silent Night’ was particularly tricky for the pitch-troubled partnership.

Smith: I think my answer (for which song was hardest to sing) is the same for both of us: ‘Silent Night.’ I know I especially, I was extremely terrible on that. I could not hit the notes.

Armstrong: [Sings Silent Night] See I can do it mild … but then we had an organ in the background so it just kinda didn’t work.

Gold-Smith: He’s no Frank Sinatra, even though he might think he is, but he can carry a tune. There were times as we were doing it where I sort of had to stop myself from chuckling or cringing.

Despite the struggles on ‘Silent Night,’ Smith claims they recorded the entire album in one take.

Gold-Smith: It might not have been one straight take from start to finish, I think we might have stopped a couple times, but we did really speed through the songs. Mostly because it was a time crunch… I think given how rushed it was it ended up turning out really well.

Armstrong: ... And then we did the hoops show and looked at each other and said I can’t believe we just did that.

The Fallout

With the album in the can, Smith and Armstrong had officially locked Jack’s OG singing partner out of the process entirely. During the course of the album, Smith makes reference to Matt Devlin’s absence, suggesting that he was off “rehearsing Bon Jovi songs” before welcoming Jones in for his cameo.

Smith: I think Devlin wanted to be part of it.

Armstrong: He was a little upset he didn’t make the cut.

Devlin: Looking back at it I had no idea that they were putting it together. I vaguely remember the conversations where I think they were kinda talking about putting it together, what have you. And of course any time that there’s a bad Christmas album being put together, why wouldn’t you wanna be a part of it? I certainly would have been the worst of the three of us there’s no doubt about it.

Smith: When there was talks about a second album, Matt was definitely in on it. He wanted to be a part of it and I feel like he definitely woulda kicked me off.

What’s most egregious about Devlin’s exclusion is the fact that the still photo backing up the most-viewed YouTube video featuring the album is not of Smith and Armstrong — it’s actually of Jack and Matt engaged in one of their sing-a-longs. However, the pure joy of the first round of listens to the freshly-pressed album seemed to repair the rift between the broadcasters.

Devlin: It was absolutely hysterical when they put that together. I was crying listening to it, it was so funny.

Armstrong: It was hysteria. I think people enjoyed it and got a lot of laughs out of it.

Smith: I thought I was better than that until I heard the CD and I am shockingly bad.

Gold-Smith: Going into this I knew I had to lower the bar — this was not going to be Stax or Mo-Town. This was just kind of a fun, light-hearted thing for them. I actually admired the fact they were willing to put themselves out there and expose themselves like this. They didn’t care that they weren’t professional singers. That takes a lot of guts.

Jack and Eric’s courage paid off. After pressing the albums by hand, one-at-a-time at home, Smith began the distribution process, with the proceeds earmarked for the Team Up Foundation.

Smith: My wife helped put all of them together and stuffing the little sleeves in those writable CDs. We mailed out a bunch, but I would bring 10, 20, 50 down to a game in a cardboard box and I’d basically say “if you’re at the game, come on down!” And people, like, would lean over and yell “ERIC! FIVE BUCKS I WANT A CD” and we just did it that way. I think we ended up saying we made roughly about 2000 bucks for the charity if memory serves correct. So, uhh, do the math.

Armstrong: That’s a lot of CDs considering how bad it is…

A few years after the initial release, the album received a second life when it was made available for digital download — with the help of Jaspreet Mangat’s wife, in fact, per Smith. Beyond its life on the internet, the participants are still reminded of their work routinely to this day.

Smith: I don’t know where my copy of the CD is. So I haven’t listened to it (recently). So the YouTube link you’re talking about — November 17th I got an email from Eric Prime, who I work with at the fan, and he said “we stumbled upon this,” and I didn’t know what the hell it was, so I clicked on the link and it was the YouTube thing. And then he wrote me back about how epically bad it was, he made a point of talking about how terrible I was.

Devlin (via DM on Thursday, Dec. 21):

Armstrong: Actually my brother in law when we go to his house every year at Christmas, he automatically pops that in. People are like “Who is that? That’s horrible? Dad that sounds like you, Uncle Jack that sounds like you!?”

It really makes it a Blue Christmas.

The Future

It’s been seven years (as of the time of writing) since ‘From Brooklyn to Toronto’s’ release. In the intervening years, Armstrong has made the move to working exclusively for TSN, while Gold-Smith left his post with The Fan and now works as a Senior Hockey Editor with The Score. A follow-up album might seem like a long shot. But it might not be the most outlandish suggestion.

Devlin: It’s hard to believe that it was 2010, that that many seasons have gone by and they haven’t followed it up! I mean that’s really what they need to do — is they should probably put one out every year. [I’d want in on it] only if Leo [Rautins] was a part of it. If I could hear Leo be a part of it then I think you know what we could have some fun.

Smith: I feel like we could do better if we ever did it again… But maybe not.

Gold-Smith: If all parties are cool with it, I definitely am. If they wanna invite me back I’d definitely be game for that.

Smith: I remember thinking “wouldn’t it be cool if we could get a player or two to sing on a track?”

Armstrong: Our team was bad at that time… if they couldn’t play they might as well be able to sing.

Smith: And I remember saying at the time if we ever did a second album, what are the odds that we could get Player X to join in. Maybe Jonas. He’s got a real quirky personality.

Armstrong: He’s got a great sense of humour. Norm’s got deep pipes.

Smith: Fred VanVleet’s kinda quiet but I think there might be something hiding in there.

Armstrong: Just to let everyone know there’s a possibility that this could be revisited for Christmas 2018. Negotiations will begin, our people and your people.

Note — It’s nine days until Christmas 2018. There have been no murmurs of any secret recording sessions. But the Raptors are back from the road on Monday... maybe, just maybe, a Christmas miracle is in the cards.