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)
Love Whitney Avalon! Her Princess Rap Battles are easily as good as some of the better Epic Rap Battles.
Da Vinci’s Notebook is great too.
Kingdom in the Sky
Title of the Song
The Poxy Boggards are fun, but usually filthy
Hey Nonny Nonny
The Ballad of Onan
Richard Cheese just covers regular songs, but it’s hilarious to hear his lounge singer take on them.
Closer (NIN)
Gin and Juice