Weird al is a rather obvious.
But Axis of awesome is also a sheer favourite of mine. their four chords song is a genius composition mashup of many iconic songs throughout the years.
Whitney Avalon is a very underrated one who does some really good and rather witty pop culture themed songs.
Least favourite: Dennis Leary (He lives up to his name)
The Arrogant Worms, and Three Dead Trolls in a Baggie. Canada stays winning.
And it’s a heave-ho, hi-ho, comin’ down the plains
Stealing wheat and barley, and all the other grains
And it’s a ho-hey, hi-hey, farmers bar your doors
When you see the Jolly Roger on Regina’s mighty shores!
(har har har, eh?)
For those that don’t know; https://www.youtube.com/watch?v=IehQRVylI0U
Though the version most people are familiar with is actually a cover; https://www.youtube.com/watch?v=8G_L9tXEwmc
(I am, begrudgingly, forced to admit that the Captain Tractor version is better)
Throw in Corky and the Juice Pigs while you’re at it.