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)
Blowfly
Amazing musician, recorded some great funk / soul records under his real name Clarence Reid. Pioneer in making songs about appreciating women.
‘Wierd world of Blowfly’ is a worthwhile documentary about him if you’re trying to get familiar.