A native of Winnipeg, Manitoba, Simmons started his career as an entertainer very early, staging neighborhood parades, circuses, and magic shows. Later, Al teamed up with fellow Canadian Fred Penner on a concert tour of Canada. The successful series lasted three years, until 1976. Penner continued the friendship into the following decades, often asking Simmons to guest star on his syndicated children's television program, Fred Penner's Place.

In the '80s, Simmons was also featured on Sesame Street, and even starred in a Canadian National Film Board movie about his "horse-cycle," Ol' Spoke. Simmons also became an Official Representative of Canada, touring Expos in Tokyo, Vancouver, and Brisbane.

Simmon's first solo effort for kids, Something's Fishy at Camp Wiganishie, was filled with eclectic, humorous songs about Lego underwear and collecting feathers. Simmons didn't write one of the most memorable of the songs on the Oak Street album; "I Want a Pancake" was a rousing rendition of an old favorite. Although the album had limited distribution outside of Canada, many of its songs were featured on children's radio and compilation albums.

In 1996, Simmons created an ode to vaudeville, Celery Stalks at Midnight. The album featured classic songs such as "Sam, You Made the Pants Too Long" and the title cut, a tune from the Depression era that concludes with "All eyes are on the potato, and the beat goes on." Typical of Simmons' fearless style, the album also included what may be the longest pop song ever recorded for kids: an eight-minute song about the life cycle of the mosquito. But Simmons' instincts paid off: the album won the coveted Juno Award in 1996.

Simmons returned to a more folk-oriented sound in 1998 with The Truck I Bought From Moe. As in his earlier releases, Simmons featured unusual songs worth re-recording, such as the Copp/Brown classic "The Dog Who Went to Yale" and "Gypsy Sock," a tango about a sock with wanderlust ("I want to run with the wild hose, where pens and pencils and the car keys go"). With Simmons at the helm, even incorrigible socks and erudite dogs seemed to work together.