Legacy Performers


Toronto — Grammy nominated, Juno Award winning, multi-platinum Singer/Songwriter, Don't Forget Me (When I'm Gone) & Someday (Glass Tiger)

Alan Frew is a multi-platinum selling songwriter, public speaker and author of the best-selling book ‘The Action Sandwich-A Six Step Recipe to Success by Doing What You’re Already Doing’. His work with Glass Tiger has garnered him five Juno Awards, a Grammy nomination and five Canadian Classic Awards in recognition of songs that have been played in excess of 100,000 times on Canadian Radio.


Award-Winning singer/songwriter for #1 hits including Carrie Underwood's "Good Girl", Rascal Flatts' "Rewind", and Jason Aldean's "Just Getting Started". Chris is also a 3x CMA Triple Play Award winner

Chris DeStefano is a singer/songwriter, producer/mixer and multi-instrumentalist based in Nashville, TN.  He is a 3x CMA Triple Play Award Winner and has co-penned over 20 hit songs for artists like Carrie Underwood, Luke Bryan, Chase Rice, Rascal Flatts, Billy Currington, Dan+Shay, Miranda Lambert, Chris Young and Morgan Evans.  Chris also is the President and CEO of Winsongs Music focused on developing songwriters and artists.


Award-winning writer of If It Makes You Happy & Everyday is a Winding Road (Sheryl Crow)

Award winning, singer-songwriter Jeff Trott has been a key member of the Nashville music community.

He has played in bands such as Wire Train, World Party, Pete Droge and Tears For Fears in addition to launching a solo record in 2001“Dig Up The Astroturf”. However, Trott's name is probably most recognizable among fans of Sheryl Crow, as he has co-written some her biggest hits including "If It Makes You Happy” "Everyday is a Winding Road” “A Change” "My Favorite Mistake”and “Soak Up The Sun”.


Nashville — Award-winning Songwriter. Hits include The Climb (Miley Cyrus) and I Drive Your Truck (Lee Brice)

Established Singer/ Songwriter, Jessi Alexander, is the writer of some the chart topping hits on country radio. Alexander has penned five #1’s including “I Drive Your Truck” recorded by Lee Brice which won Song of the Year from the 2013 CMA Awards, 2014 ACM Awards, and 2013 NSAI Awards. Additional #1’s which include Blake Shelton’s “Mine Would Be You” and “Drink On It”.


Multi-platinum, Juno Award-winning Rock icon and inductee of the 2021/22 Canadian Songwriters Hall Of Fame

Kim Mitchell is a Canadian rock icon who has sold more than 1.5 million records in Canada, earned 17 Juno Awards nominations, and, in 2021, was inducted into the Canadian Songwriters Hall of Fame.


Okotoks, AB — Canadian Country’s Rising Star. Great new single, Dreamer Kid

There’s a classic timelessness and a sense of poise to Maddison Krebs that you won’t often find in someone of her era. The 25 year old singer-songwriter, native to Southern Alberta, has spent the last 3 years in Nashville honing her musical abilities and song-craftsmanship with intention to create depth, meaning, integrity, and love behind her music.


Toronto — Multiple Platinum Artist/Songwriter - Marina Del Rey (Marc Jordan) and Rhythm of My Heart (Rod Stewart)

Marc was born in Brooklyn NY son of singer Charles Jordan and grew up in Toronto Canada. In 1978 Marc was signed to Warner Music in Burbank California by Steely Dan Producer Gary Katz. Jordan spent 16 years in LA writing songs for and with Diana Ross, Chicago, Kansas, Manhattan Transfer, Kenny Loggins, Amanda Marshal, Amy Sky, Bette Midler, Natalie Cole, Roch Voisin, Canadian Tenors. Shawn Colvin, Sheena Easton, Olivia Newton John, Joe Cocker, Bonnie Raitt, Josh Groban, Cher and Rod Stewart including the world wide #1 hit Rhythm of My Heart.


Vancouver — Lead Singer of 54•40 - Hits include I Go Blind and Ocean Pearl

As lead singer and chief songwriter of 54•40, Neil Osborne has achieved critical acclaim, released more than a dozen albums and weathered the fickle music business for more than three decades. He is known primarily as a rock musician but is also an accomplished producer often taking the production reins of 54•40 albums and is also a songwriter of amazing depth and clarity.


Chetwynd, BC — Popular, BC-born, singer/songwriter. Recent singles and Country Music Chart hits include “I Don’t Wanna Fall in Love Anymore” and “Blame the Wine”

Teigen Gayse is a Metis singer-songwriter whose music is fresh and familiar, hitting on deep and relatable topics.  She grew up in Chetwynd, BC.  A small town of 3000, affectionately known as “Little Prairie”.  Music was her escape from the forestry, oil & gas, mining and ranching environment she was surrounded by.  This singer/songwriter’s lyrics and melodies are catchy.


Nashville — Grammy Winner - Live Like You Were Dying (Tim McGraw)

Inducted into the 2017 class of the Nashville Songwriters Hall of Fame, award winning songwriter, Tim Nichols, has been writing hit songs and entertaining audiences for over two decades. A veteran in the country music industry, he's become one of the genre's most respected and well liked members. He's known for an easy-going, honest manner, creative lyrics and a comedic banter onstage.


Nova Scotia — 8x Juno Nominated Singer/Songwriter - Lead Singer of The Northern Pikes - Hits include She Ain't Pretty

Bryan Potvin is best known as a singer/songwriter, guitarist, and founding member of The Northern Pikes, the iconic Canadian rockers from Saskatoon. Bryan’s love of music began early. In the summer ‘75, at the age of 12, he worked on a potato farm in Victoria, B.C. to earn enough to buy his first guitar, a Japanese Mann Les Paul Standard.


Hamilton, Ontario — Lead Singer of Legendary CDN Rock Band Teenage Head - Hits include Some Kinda Fun & Let’s Shake

Songwriter Dave Rave, lead singer for noted Canadian punk band Teenage Head, dubbed “Canada’s Nick Lowe”, has rocked the world from Hamilton, Ontario all the way to Russia. New York City-based, Rave can lay claim to being the first Canadian artist (The Dave Rave Group) signed to a Russian label (Melodiya). Teenage Head crashed onto the Canadian music scene with a couple of riotous appearances at the Last Pogo show at Toronto’s Horseshoe Tavern in 1978.


Alberta — Multi Award Winning Singer/Songwriter, #1 Hits - Dive Bar & When Your Lips Are So Close (Gord Bamford)

Alberta-raised Gord Bamford, stands as one of the most decorated artists in Canadian country music with an impressive 26 Canadian Country Music Association (CCMA) awards, multi JUNO nominations and the only two-time winner of Nashville’s Country Music Association (CMA) Global Country Artist of the Year award.


Toronto — Award Winning Singer/Songwriter - Somebody Gonna Get Hurt (Jessica Mitchell), Courage (Celine Dion) and Workin' on Whiskey (Trisha Yearwood)

Singer-songwriter Jessica Mitchell has been lauded as ‘country’s Adele’ and likened to Sheryl Crow, and much like them, her genre-bending vocals and tone are universally appealing. She is, at heart, a storyteller– an open book, inspired by the raw honesty and storytelling nature of the genre.


Alberta — Multi-Award Winning Singer/Songwriter - Single White Female (Chely Wright), Complicated (Carolyn Dawn Johnson), Georgia (Carolyn Dawn Johnson)

After inking a record deal with Sony’s Arista Nashville in 2000, Johnson produced music of her own with the release of her debut album titled Room With a View. The critically acclaimed project spawned the Top 5 smash “Complicated,” as well as other hit singles such as “Georgia” and top 10 “I Don’t Want You to Go.” Albums to follow included Dress Rehearsal in 2004, her independently released Love & Negotiation in 2006 and Love Rules in 2010. Johnson also criss-crossed the country on many high-profile tours as the opening act for the likes of Reba McEntire, Alan Jackson, Kenny Chesney and Keith Urban.


Fan Favorite X-Factor UK 2018

Maybe it’s something in the Caribbean water that's producing music's newest hottest stars and songs. Hailing from the small Caribbean island of Anguilla, Deanna jumps right in the fray with her stunning performances at X Factor UK. With outstanding comments from all judges, to becoming a fan and media favourite while garnering major press, Deanna sang her heart out and made it to the final stages of the show.


Ontario — Grammy Nominated Songwriter/Recording Artist - Mine Would Be You (Blake Shelton) and That's How I Wanna Go Out (Deric Ruttan)

Deric Ruttan is a Grammy-nominated, Nashville-based singer/songwriter and a Canadian country music artist. The writer of multiple #1 country songs, Deric was raised just outside Bracebridge, Ontario, on land where his great grandfather made moonshine in the 1930’s. It was the perfect backdrop for the singer/songwriter, who grew up listening to everything from CCR to Gordon Lightfoot to Johnny Cash. After touring with several country bar bands, Deric moved to Nashville, where his unique outlook and delivery attracted the attention and praise of songwriters Don Schlitz, Steve Earle, and Steve Bogard.


Toronto — Juno Nominated Singer/Songwriter - Back Where You Belong (38 Special)

“To say that music has been a huge part of my life, would be an understatement.” That’s what Canadian singer/songwriter GARY O’ would tell you. Son of a famous bandleader, he was raised on a strict diet of Ray Charles and The Beatles and the great melodies that came from that music. Great influences for a future songwriter. Before venturing out on his solo career, GARY was an accomplished session guitarist and toured North America with the very first Beatle clone band (Liverpool), which became the Broadway hit “Beatlemania”. First attempt at writing a song resulted in the radio hit “Easy Love” for the band Aerial.


Toronto — Juno Award Winning Singer/Songwriter - Keep it Simple (James Barker Band)

Gavin Slate is a Juno Award winning songwriter from Toronto, ON and currently living in Nashville, TN. He has co-written 11 Gold Certified singles, 17 Top 10s and two #1 songs for artists including The James Barker Band, The Reklaws, Jade Eagleson, Tim Hicks, Kira Isabella, Cold Creek County, Sons of Daughters etc. In addition to this, he has also had songs placed as an artist himself in TV shows including NBC's Rookie Blue, ABC's Saving Hope and most recently had his song featured in the holiday campaign for Stella Artois.


Nashville — Award Winning Hit Singer-Songwriter - There is No Arizona and When I Think About Angels

Since the release of her debut album Jamie O'Neal has been impacting country music with her soulful voice and the immense amount of passion behind every word she sings. O’Neal became a household name with her single, “There Is No Arizona,” which set her path to stardom on fire with multiple No. 1 hits and 2 top 5 records as well as many award accolades. “From a young age, I had a bird’s eye view as entertainers like Johnny Cash, Dolly Parton, Willie Nelson and Crystal Gayle performed,” she says. “I watched from the side of the stage at the way they connected with a crowd, and that’s what made me want to be a performer."


Toronto — Singer/Songwriter - Courage (Celine Dion) and Won't Back Down (Eminem)

Chart-topping Canadian songwriter Liz Rodrigues, who has six songs on Celine Dion’s new album, Courage, has also written multiple songs for Eminem and countless other popular music artists. The versatile topliner takes a more personal approach for relationship and emotional based adult-contemporary pop lyrics, but looks outside for the storytelling style required in most hip hop. A singer long before she became a writer, Liz is also the voice on the demos.


Nashville — 2019 Nashville Songwriters Association - Songwriter of the Year, Waitin' on a Woman (Brad Paisley) and A Little More Country Than That (Easton Corbin)

Wynn came to love country music at a very young age. He discovered his father’s collection of classic country albums. He even traded his big brother’s “Grand Funk Railroad” for a copy of Jimmy Dean’s “Big Bad John”. He still has a scar to prove it. Around the age of 14 a neighbor named Ned Smith showed him a few chords on an old guitar. As soon as Wynn learned a few chords, he began to write his own songs. Wynn says Willie Nelson taught him the rest from the “Red Headed Stranger” album.


Nashville — Hall Of Fame Inductee - Blue Clear Sky (George Strait) and Southern Voice (Tim McGraw)

Since his first #1 in 1983, Hall of Fame Songwriter Bob DiPiero has been responsible for an uninterrupted string of country music hits. One of Nashville’s most prolific and consistent songwriters, Bob possesses a humble drive to keep learning and stay relevant. He has had over 1,000 songs recorded by other artists, countless hit singles, and an astounding 15 #1 hits. His songs have been featured in TV shows, commercials and movies. Among his countless awards are 50 BMI Million-Air honors, multiple Songwriter of the Year awards and 2 consecutive Triple Play awards for 3 #1 songs within a 12-month period.


Nashville — CMA and ACM “Song of the Year” Winner, I Drive Your Truck (Lee Brice)

Jimmy Yeary has been writing songs in nashville for 25 years. After a short period in 2001 with Atlantic records as an artist, jimmy decided to focus all of his attention on songwriting. Jimmy has quickly become one of Nashville's most sought after songwriters, with 8 top tens, 7 of which have reached #1.


Toronto — Award Winning Broadcaster - The Paul McGuire Show

A pop-culture junkie, Paul McGuire spent his childhood devouring movies, TV, comic books and music. Inevitably, he chased a career in the entertainment industry. A few commercials gigs and small TV roles paved the way for a hosting job on a children’s game show that aired on “Canada’s Nickelodeon,” YTV. Paul moved on from YTV to work at Canada’s largest network, CTV, as host and producer of Canada’s first entertainment magazine show, ENow.


Kelowna, BC — Multi Award Winner and Host of The Casey Clarke Show

Casey Clarke started his career in 1989 in Westlock AB working on 1370 CFOK from there a stop in Whistler/Squamish at Mountain FM then over to Vancouver to work for The Satellite Network's "Country Coast to Coast " channel.


Valeria Tait is a long time resident of the Okanagan and, as the former General Manager and winemaker at Bench 1775, a founding sponsor of 97 South Song Sessions. Tait has been a strong supporter of the performing arts, hosting numerous live events combining music and wine culinary experiences. Tait has also been active in the community as a board member of the Penticton Art Gallery.