[5] Humour Me was nominated for a Juno Award, in the "Best Roots or Traditional Album" category.

[2][9] Jerry Douglas played dobro on the album; Dave Pomeroy, Jim Horn, and Béla Fleck also contributed.

[16] The Washington Post called the album "strictly mid-level stuff," but conceded that it was "nevertheless chock-full of songs that combine insinuating melodies and rhythms with tender sentiments so deftly handled that they never sound as trite as they might appear on paper.

"[18] The Ottawa Citizen stated that the music ranges from "earthy front porch blues and cafe folk to the odd lounge lizard croon.

"[19] AllMusic wrote that "Humour Me lacked the depth of Winchester's best work, but it was easily on a par with his substantial body of craftsmanlike music of the mid-'70s... His voice remained warm and supple.