Raymond Wilson Drain

Raymond “Ray” Wilson Drain, of Portage la Prairie, Manitoba, passed away peacefully on May 14, 2026, at Portage District General Hospital at the age of 97 years. Ray was predeceased by his beloved wife, Doreen, and was the last surviving of 11 children.

Born on September 4, 1928, Raymond “Ray” Drain grew up with a love for trucks, music, and adventure. As a child, he spent hours “playing truck driver,” proudly pushing two tires around the yard while the other kids made do with one, because Ray insisted, he was the only one who knew how to drive truck properly. One of his favourite childhood stories was riding his pony to see a plane that had crash-landed in a nearby field, only to have the pony bolt home when the engines restarted, leaving Ray to walk back through the muddy field all the way home.

Music was a lifelong passion for Ray. He loved singing and playing the banjo and guitar, though his first stage performance at North Ridge School ended with him bending so far over that he fell off the stage. In later years, he became known as the “King of the Saddle,” performing live every Saturday afternoon at the Capitol Theatre on CBC radio broadcasts. He often shared the story of meeting Hank Williams in an elevator and joking that Hank had left “ashes on his shoulder” after accidentally brushing him with a cigarette.

Ray met the love of his life, Doreen, while she was still in high school. Though she politely declined his offer to buy her an ice cream cone, Ray remained determined, and the two were married two years later. Together they raised their family; Kim, Wayde, Vince, and Quinn, while farming cattle, grain, and sugar beets. Ray also spent many years driving truck for Manitoba Highways, paving roads across small towns throughout the province.

Known as “Sugar Ray” or “Mr. Sugar,” Ray earned the Sugar Beet Cup in 1972 for the highest sugar beet yield per acre. His band, The Parking Lot Pickers, became known as “Sugar Ray and the Men on the Beet.”

Ray also carried on a long family tradition in the wood business, a trade passed down from his father, who hauled logs into Portage by horse team to be cut and sold. Ray’s hardworking spirit, humour, storytelling, and love for music and family will be fondly remembered by all who knew him.

So many great memories!

Wayde Drain

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One of my favourite memories of Ray was the many years we spent hauling wood together. So many early mornings, long days, and evenings were shared with Ray, Wayde, and I. We would start each day over a cup of tea, planning what supplies we needed — chains, fuel, oil for the chainsaws — along with plenty of jokes, laughter, and appreciation for the great outdoors.

At the end of the day, we would sit back with a cold beer or two, talking about everything that went right and the moments that didn’t quite go as planned — like the time a branch snapped back and smacked me in the face, or the look on Ray’s face when a tree fell the wrong way.

Through it all, we survived, laughed hard, and truly had the time of our lives. Those memories will always hold a special place in my heart.

I love you Ray…

Janice Anamah

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Dad always enjoyed getting together on Friday and Saturday evenings after a hard day’s work in the yard or out cutting wood. Fridays were spent in the sunroom, while Saturdays were usually around the round table in the garage. There was always a couple of cold beers, plenty of jokes, good music, and lots of laughter.

Dad always wanted to know what everyone was doing in the yard — he liked to stay one step ahead, and somehow, he usually was. Those moments together, filled with hard work, humour, and family, became some of our most cherished memories.

Dad, now you are reunited with Mom, and although you are deeply missed, you have left us with a lifetime of wonderful memories. You will forever remain in our hearts.

Vince and Shelly Drain - Ryan, Susie and kids

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Where do we even begin with our silly grandpa?

Grandpa brought laughter everywhere he went. Anytime we were around him, he always had a new joke to tell — and while they were not always exactly PG, they always had us laughing. There was never a dull moment with him, and one of our favourite things was simply sitting and listening to the stories he would share while enjoying either a cup of tea or a cold beer.

Our love for bluegrass music exists because of Grandpa. We grew up surrounded by live music, from parking lot pickers playing at various parties to annual camping trips at Shady Oaks. Those weekends became some of the most special memories of our childhood, and even today, hearing bluegrass music instantly brings us back to him and those fond memories.

Something that no one will forget about him is his quirky way of letting you know he loves you or cares about you, by pinching your arm, requesting cheek kisses, or simply telling you to “F*ck Off”.

Above all else, Grandpa was someone who made people feel happy just by being around him. He leaves behind stories, laughter, music, and memories that will stay with us forever. We love him deeply, and we know a part of him will always live on every time we hear a bluegrass song play.

With love from Chelsea Tan and Krystal Drain – your ‘favourite’ granddaughters ❤︎

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We would like to extend our heartfelt thanks to all of the doctors, nurses, health care aides, and allied health staff at Portage District General Hospital for the care, compassion, and support they provided to Raymond and our family during his time there. Your kindness and dedication will always be deeply appreciated.

A memorial service will be held at St. Mary's la Prairie Anglican Church on Friday, May 22, 2026, at 2:00 p.m., led by Rev. John Dolloff. Interment will take place at Hillside Cemetery Columbarium. Followed by a celebration of Ray's life at the family farm, everyone is welcome.

The service will be livestreamed. To register and view please click the link below.

A tree will be planted in memory and cared for by McKenzies Portage Funeral Chapel. www.mckenziesportagefuneralchapel.com