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)
Weird Al, of course… he’s an effing genius. But so is Tom Lehrer. He was a comedy musician popular through the '50s and '60s. He’s also credited for inventing the Jello shot as a way to sneak alcohol onto his military base.
TIL about the jello shot. My favorite story about Tom Leherer is when rapper 2 Chainz wanted to sample his song “The Old Dope Peddler”.
Lehrer’s reply read “I grant you motherfuckers permission to do this. Please give my regards to Mr. Chainz, or may I call him 2?”