Toronto folk-roots-rockers, The Skydiggers, performed at the West End Cultural Centre on Friday, bringing joy with Christmas tunes and more from an extensive catalogue.
Scattered throughout their show of original tunes and covers, they played songs from their Angels CD, which started out as a 5-song EP of Christmas songs a year ago. Like a healthy child, the EP grew and expanded into an 11-song CD this year. The band did two sets Friday night.

The scaled-down version of the Skydiggers: Michael Johnston, Josh Finlayson, Jessy Bell Smith and Andy Maize.
The band has been together since 1987 and released their first album in 1990. They have released 16 albums over the years and have played concerts the week before Christmas at the legendary Horseshoe Tavern in Toronto for many years.
The Christmas concerts were started by the Tragically Hip in the 80’s and ran up until 1987 when that band became really big. The Skydiggers carried on the tradition of the Christmas concerts, playing Dec. 27 as the Hip did, but eventually switched the date to a week earlier.
Four members of the band visited Winnipeg for this show. Lead vocalist (and trumpet when it works) Andy Maize, Josh Finlayson on guitar, Michael Johnston on keyboards, and singer Jessy Bell Smith. They were joined on stage by special guests Jeffrey Hatcher, Keri Latimer of Nathan, and singer-songwriter Kate Friesen.
The band flew in from Toronto on Friday and dropped into the Winnipeg Free Press Cafe where they were interviewed by Free Press writer Geoff Kirbyson, in between the three songs they performed. They played ‘Remember Me,’ ‘Church Bells Ringing on Dundas Street’ and a John Prine cover, ‘Christmas in Prison’ which Jessy Bell Smith sang.
The lunchtime set was a nice little appetizer for what turned out to be a tasty show in the evening.
West End Artistic Director, Jason Hooper, came on the stage shortly after 8 p.m. to introduce the band. It’s nice the WECC allows them to play here; their show in the ’90’s saw fans dancing so hard the floor collapsed. Sort of the other end of the spectrum to raising the roof; instead, they blew out the floor.
The band came on with Andy Maize talking about their good friend Kevin Walters who passed away from cancer in June. He mentioned proceeds of the show will go to the Kevin Walters Memorial Fund. Mr. Walters was a Winnipeg promoter of musical and cultural events.
The first song they did was the beautiful and touching Pretenders tune, ‘2000 Miles,’ which had Maize and Smith sharing vocal duties. Next up was ‘Anything For You’ and it seemed like the band was prepared to do anything to show us a memorable evening.
Thoughout the evening, Michael Johnston alternated between the large piano on the stage and his Nord keyboard, which also provided violins and cellos sounds for a few songs. He even got the sound of a Hammond organ at times out of that little keyboard.
Maize commented the Duhks will be playing the WECC on Jan 8, which is David Bowie’s birthday and also would have been Elvis Presley’s 80th birthday. This got the singer thinking about karate, which made him strike a few karate poses. Maize was very entertaining as he engaged the audience between songs.
Josh Finlayson sang ‘Horseshoe Bay’ and Andy Maize tried to play his uncooperative trumpet (probably affected by the weather). After the song Maize said he would be posing with his trumpet for pictures for a toonie and donating it to the foodbank, to which Finlayson joked, “or for trumpet lessons.”
Next Jessy Bell Smith was featured on vocals for the John Prine cover ‘Christmas in Prison.’ She did the song justice with her emotional rendering of the song. This song was followed by a Byrds cover written by the late Gene Clark, ‘Here Without You.’
Singer songwriter Kate Friesen joined the band with one of her songs ‘Late in the Evening’ and helped the band on their song ‘Hello Beautiful Life.’ Hello beautiful harmonies is all I can say about those songs.
Then they pulled out a song from, in Maize’s words, “the best songwriters in the House of Commons…Charlie Angus and Andrew Cash,” ‘Church Bells Ringing on Dundas Street.’ I wish more Members of Parliament could have as much clarity as these guys.
After the 50-minute set and an intermission, the band came back on and dedicated the song ‘Remember Me’ to Kevin Walters. Josh Finlayson put down his acoustic guitar and played piano beside Michael Johnston on keyboards for the next song ‘Twilight.’
Nathan’s Keri Latimer came up on stage with her guitar for two songs, ‘Cottonseed,’ which she wrote for O Susanna and a Wilco song, ‘Jesus, Etc.’ She dedicated the Wilco song to her friend Susan whose wedding she was supposed to sing the song at but had laryngitis, so Michael Johnston sang the song with his accordion.
Jessy Bell Smith sang ‘Dear Henry’ next in that wonderful style that is uniquely hers. After a couple more songs, Jeffrey Hatcher took to the stage for a song written with fellow Winnipegger David Briggs ‘Precious Rays.’ Then he played “a song we all remember from kindergarten,” Nick Lowe’s ‘Cruel to be Kind.’
After the second set of about 50 minutes, the band left the stage to thunderous applause. They came back for a three song encore with Smith singing ‘Rambling On,’ after which Maize invited all of their special guests back to the stage to help them on the next song adding, “you (the audience) are our guests as well, so you’re welcome to join us for a rousing rendition of ‘Slow Burning Fire.'” It was hard to contain the slow burning fire as the audience and performers were clearly smoking hot.
Andy Maize thanked everyone for a wonderful evening ending with a song that “delivers a message about looking after those less fortunate than oneself,” ‘Good King Wenceslas.’ Maize’s trumpet was not cooperating once again, forcing him to put it down once again exclaiming, “I suck.” No you don’t Andy, your trumpet sucks when it should blow.
A wonderful evening of original songs and covers with lots of toe-tapping and laughs along the way. The Skydiggers songs are certainly in the same class as some of the singer songwriters they covered throughout the evening in terms of relating good stories in a thoughtful and graceful fashion.
All photos by Doug Kretchmer
Click here to see the Skydiggers’ Free Press Cafe performance.
Setlist:
SET 1
1. 2000 Miles (Pretenders cover)
2. Anything For You
3. Shimmy Up Those Words
4. Horseshoe Bay
5. Poor Little Jesus
6. Feel You Closer
7. Christmas in Prison (John Prine cover)
8. Here Without You (Bydrs cover)
9. Late in the Evening (Kate Friesen)
10. Hello Beautiful Life (with Kate Friesen vocals)
11. Elizabeth Josephine
12. Chuch Bells Ringing On Dundas Street
(Andrew Cash and Charlie Angus cover)
SET 2
1. Remember Me
2. Northern Shore
3. Twilight
4. Cottonseed (Keri Latimer)
5. Jesus, Etc. (Wilco cover)
6. Dear Henry
7. Strong Disinclination
8. Just My Heart
9. Precious Rays(?)
(Jeffrey Hatcher/ David Briggs)
10. Cruel to be Kind (Nick Lowe cover)
11. I Will Give You Everything
12. A Penny More
ENCORE
1. Rambling On
2. Slow Burning Fire
3. Good King Wenceslas (traditional)