If you’re looking for backstage stories about Lady Gaga, Bob Dylan, U2, Amy Winehouse, Sharon Jones, or Ed Sheeran, consider buying Ian Hendrickson-Smith a drink when he visits Vancouver next week; the saxophonist has worked with them all. When it comes to dishing the dirt in an on-the-record interview, however, the New York resident turns out to be blessed with as much tact as he has talent—or else his memory is starting to go after spending more than 700 days on late-night TV.

“It’s tough, you do it so much,” says Hendrickson-Smith, who’s the guy sporting a flat cap and a tenor sax that Tonight Show devotees will have noticed on-stage with Jimmy Fallon and his house band, the Roots. “If you asked me who was on the show yesterday, I would have no idea.”

Picked for the gig after working with Roots bandleader Ahmir “Questlove” Thompson on soul star Al Green’s 2008 album, Lay It Down, Hendrickson-Smith is less reticent, or forgetful, when it comes to the details of his high-profile job.

“We tape at 5 o’clock every day, Monday through Friday, but on Monday we get a schedule of what guests are appearing over the week and what they’re promoting,” he explains, on the line from a festival show with the Roots in Burlington, Vermont. “And then Questlove goes through that and picks whatever music we’re going to play to walk them onto the set.…We spend maybe two minutes on each cue; one of the challenges of the job is that you have to learn a lot of music really quickly and efficiently.

“There’s no charts,” Hendrickson-Smith adds. “Nothing is really ever spoken about.…You have to be quick on your feet and your ears have to be pretty strong.”

This impromptu approach will also be on the menu when Hendrickson-Smith joins an all-star cast of Vancouver jazz musicians at Frankie’s Jazz Club; with no time for rehearsals, the quintet will have to suss out his mix of blues, standards, and originals on the fly. One difference, though, is that he’ll get to play his first love, the alto sax, as opposed to the tenor and baritone horns he usually deploys on money gigs. “It’s the instrument that I put the most time in on,” he says. “A lot of my favourite saxophone players are alto players: Jackie McLean and Bird [Charlie Parker] and Johnny Hodges and Charles McPherson.”

Split the difference between those swing-to-bop legends and the work that Hendrickson-Smith does with the Roots, and you’ve got a clue to his character: he’s got an old soul and a curious mind, a combination that serves him well in his other job as a graphic designer. Most notably, he devises the majority of the album covers for Vancouver’s own Cellar Live imprint, a role that came about through his friendship with his fellow saxophonist, local jazz impresario Cory Weeds. Weeds, in fact, is one of the reasons Hendrickson-Smith will be playing alto here: the label boss and Coastal Jazz programmer will be performing on tenor in the band, which also includes pianist Miles Black, bassist Jodi Proznick, and drummer Jesse Cahill.

The relationship dates back to when Weeds heard and loved Hendrickson-Smith’s 2003 debut, Up in Smoke!, and suggested they go for coffee. “We met up in New York and became fast friends because we both love the same things,” Hendrickson-Smith says of his B.C. counterpart. “And I ended up marrying his bar manager and having a love affair with Vancouver, so it’s a long but simple story!”

Ian Hendrickson-Smith plays Frankie’s Jazz Club on Wednesday (August 30).