Recording: Holy Oak Family Singers

Artist: Holy Oak Family Singers

Songs: Greenfields [The Brothers Four cover] + The Way You Look Tonight [Betty Carter cover] + Madame George [Van Morrison cover]

Recorded at The Tranzac's Southern Cross Lounge (Holy Oak Family Singers present), May 6, 2026.

Holy Oak Family Singers feat. Luka Kuplowsky & Robin Dann - Greenfields

Holy Oak Family Singers feat. Robin Dann - The Way You Look Tonight

Holy Oak Family Singers feat. Ivy Mairi - Madame George

With my work schedule the way it is, it's a rare treat to get to see the Holy Oak Family Singers in action. Unsurprisingly, their montly showcases have become local Events of Note, with the Southern Cross jam-packed very early on. Once one reaches a certain age, an event called "Our Parents' Tapes" might be attended with apprehension, as the gap collapses towards "tapes I had". We're not quite there yet, and in any case, the group brought a pretty wide range of formative we-listened-to-this-in-the-car memories.

Recording: Holy Oak Family Singers

Artist: Holy Oak Family Singers feat. Ryan Driver / Alex Lukashevsky / Dorothea Paas / Luka Kuplowsky

Songs: Picture a World / Bein' Green / The First Time It Happens / Everybody Eats [all composed by Joe Raposo]

Recorded at The Tranzac's Southern Cross Lounge (Tribute to Joe Raposo), July 3, 2024.

Holy Oak Family Singers feat. Ryan Driver - Picture a World

Holy Oak Family Singers feat. Alex Lukashevsky - Bein' Green

Holy Oak Family Singers feat. Dorothea Paas - The First Time It Happens

Holy Oak Family Singers feat. Luka Kuplowsky - Everybody Eats

The name Joe Raposo might not ring a bell, but chances are good you've got some of his songs lodged in your brain. One of the key writers in the classic Sesame Street/Muppets era, he not only composed the Sesame Street theme, but piles of instantly-familiar tunes, including "C is for Cookie", "Doin' the Pigeon", "Would You Like to Buy an O?", and "Sing" — as well as a fair few other TV themes. That meant there was plenty of material for the usual mix'n'match insta-ensembles at H.O.F.S.' regular night of musical tribute. The best results came when the singers mined the vein of bummed-out melancholy that's just below the surface of many of these songs — but the bursts of pure ebullience worked pretty swell too (Alex Lukashevsky tackling the Three's Company theme was everything you could hope for).

[Do note that H.O.F.S. are taking August off! You'll find them back in the Southern Cross on the first Wednesday in September.]

Recording: Holy Oak Family Singers

Artist: Justin Orok & Maggie Keogh / Holy Oak Family Singers

Songs: Summer's End [John Prine cover] + Ever New [Beverly Glenn-Copeland cover]

Recorded at The Tranzac (Southern Cross Lounge), August 2, 2023.

Justin Orok & Maggie Keogh - Summer's End

Holy Oak Family Singers - Ever New

Celebrating "The Songs of Summer", this evening with the rotating cast of H.O.F.S. guests and regulars essayed, as usual, a mix of hits and deep cuts, stripping things back to their essential songerwriterly cores. (And proving, once more, that no songs are too uncool to be reclaimed, as Ben Gunning showed on an astoundingly-refreshing take on Don Henley's "The Boys of Summer".) Nursing a broken arm and unable to play guitar, host Luke Kuplowsky played some one-handed piano in a spare setting of the McGarrigle's "Saratoga Summer Song", but also pulled together an impromptu ensemble for a couple set-closing pieces, including this Beverly Glenn-Copeland song with backing from Evan Cartwright, Justin Orok and Ted Crosby.

[Maggie Keogh and Justin Orok are half of Andrew Downing's Utopia Ontario, who will be playing The Rex next Monday (August 28th). The Holy Oak Family Singers will be back on at the Tranzac on Wednesday, September 6th.]

Recording: Holy Oak Family Singers

Artist: Carlyn Bezic with Joseph Shabason + Danika Vandersteen & Aiya McNee + Madelyn Kirby & Luke Robinson + Luke Kuplowsky & co.

Songs: Stay Loose + Steel Rail Blues + Saturday Clothes + A Lesson in Love [Gordon Lightfoor covers]

Recorded at The Tranzac's Southern Cross Lounge (Holy Oak Family Singers present), June 7, 2023.

Carlyn Bezic with Joseph Shabason - Stay Loose

Danika Vandersteen & Aiya McNee - Steel Rail Blues

Madelyn Kirby & Luke Robinson - Saturday Clothes

Luke Kuplowsky & Co. - A Lesson in Love

This gathering of the Holy Oak Family Singers was themed as a tribute to recently-passed icon Gordon Lightfoot, a songwriter with whom this loose collective has a longstanding connection. Once more "later Gord" (especially East of Midnight) was tackled with as much zeal as the more well-known early material, though for this show the more elaborate backing band was replaced by a stripped-down rotating crew of musicians.

[This month's HOFS timeslot — which is tonight (July 5th) — will instead see Luke Kuplowsky joined by Felicity Williams, Anh Phung, Josh Cole, and Alex Lukashevsky for two sets of his own songs + poetry interpretations.]

Recording: The Holy Oak Family Singers

Artist: The Holy Oak Family Singers

Songs: I Believe [Loretta Lynn cover] + Wrecking Ball [Emmylou Harris cover]

Recorded at The Tranzac (Southern Cross Lounge), October 9, 2022.

The Holy Oak Family Singers - I Believe

The Holy Oak Family Singers - Wrecking Ball

This time out, the HOFS was essentially a songwiters' circle convened by Luke Kuplowsky, Thom Gill and Alex Lukashevsky — plus a few friends called up to sing some tunes, natch. The hosts completed the first round robin, where Kuplowsky paid tribute to the memory of Loretta Lynn with a rendition of a song that she covered. A bit later on Ivy Mairi also contributed a cover-of-a-cover, with a sweet rendition of Neil Young's "Wrecking Ball". Showing the back-porch spirit of the night, I left the full lead-in here, where you can feel their musicians feeling the way into it, and Mairi a bit unsure of the key at the start before falling right into place.

Recording: The Holy Oak Family Singers

Artist: The Holy Oak Family Singers

Songs: That's What Makes You Strong [Jesse Winchester cover; Thom Gill vox] + Dear Darling [Mary Margaret O'Hara cover; Ivy Mairi vox] + I Don't Know [Kate and Anna McGarrigle cover; Alex Samaras vox] + Thirty [The Weather Station cover; Thom Gill vox] + Runs in the Family [The Roches cover; Robin Dann, Felicity Williams, Alex Samaras vox]

Recorded at The Tranzac (Southern Cross Lounge), February 20, 2020.

The Holy Oak Family Singers - That's What Makes You Strong

The Holy Oak Family Singers - Dear Darling

The Holy Oak Family Singers - I Don't Know

The Holy Oak Family Singers - Thirty

The Holy Oak Family Singers - Runs in the Family

A really wonderful night, once more bringing together this loose aggregation of immensely-talented musicians that once congregated at the much-missed Holy Oak. The special occasion this time was a milestone birthday for Luke Kuplowsky, who got to pick the setlist, populating it with some of his mournful/joyful favourites. As always, the crew ranged through the songbooks of the artists they'd paid tribute to in the past (Gordon Lightfoot, Joni Mitchell, Arthur Russell in addition to the ones posted above) and a few special one-offs, like the especially-relevant Weather Station tune. And as always, there were a series of friends rotating in and out of the backing band and vocalists' chairs. Truly a really special time, and worth remembering these days as to why we used to gather together (and hope to someday again).

Recording: The Holy Oak Family Singers

Artist: The Holy Oak Family Singers

Songs: Stay Loose [vox by Ben Gunning] + Only Love Would Know [vox by Felicity Williams + Thom Gill] + If You Could Read My Mind [vox by Tamara Lindeman] + I'll Tag Along [vox by Luke Kuplowsky] [all songs composed by Gordon Lightfoot]

Recorded at The Burdock Music Hall, August 13, 2018.

The Holy Oak Family Singers - Stay Loose

The Holy Oak Family Singers - Only Love Would Know

The Holy Oak Family Singers - If You Could Read My Mind

The Holy Oak Family Singers - I'll Tag Along

You never know what you have 'til it's gone. When the beloved Holy Oak was in full swing, "family" events like this were a regular occurrence, with some of the locals who used it as their hub banding together to cover musicians ranging from Prince to Mary Margaret O'Hara. The bonds of comradeship have transcended the loss of the venue, but events like this are a bit rarer on the ground these days. It has to be said that this was entirely too good a show for a Monday night, but it just might be impossible to gather these busy pros together on any other night of the week.

The instrumental core — Evan Cartwright (drums), Ben Whiteley (bass), Christine Bougie (lap steel), Ben Gunning (electric guitar), Luke Kuplowsky (acoustic guitar) and Thom Gill (keyb) — served as session aces for an all-star team of vocalists, including the latter three instrumentalists plus Tamara Lindeman, Felicity Williams, Robin Dann and Alex Lukashevsky. There were plenty of hits essayed, from "Every Highway" to "Rainy Day People", but the group here dug deeper as well, showing a special affection for the less-popular 80's Gord, including his '86 East of Midnight album, and demonstrating that the craft and wisdom in those compositions is on par with the better-known stuff.