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)
Jonathan Coultan is my favorite singer-songwriter, ever. He’s drifted away from “comedy” songs recently, but he’s still fantastic. He’s able to perfectly straddle funny and sad, somehow.
He’s had a few brushes with more widespread notoriety, too: he wrote “Still Alive” and “Want You Gone” for Portal 1 & 2, the opening song to the show “Brain Dead,” the theme song to RiffTrax, and a great cover of “Baby Got Back” that Glee ripped off without crediting him.
Highly recommend!!!