Easy Mode:

Definitely 2 of my favorite Weird Al songs that I don’t really hear people ever talk about:

Don’t Download This Song, and Virus Alert.

Hard Mode:

I don’t listen to non-Weird Al parody songs anymore and haven’t since late middle school to early highschool, so I got none in my head anymore.

The Bad Lip Sync version of Gotye (Kicked Your Monkey And I Used Your Goat) kinda always comes to mind

https://youtu.be/PV0_lJpPFOo

• Y.O.D.A. - YODA (Weird Al)
• Hello Muddah, Hello Fuddah (Alan Sherman), based on a song from the opera La Gioconda

I cant hear American Pie without it turning into Weird Al’s The Saga Begins

Nanobot by A Capella Science. The whole channel is pretty good, but this song just shines above the pack. Shivers every time:

https://www.youtube.com/watch?v=ObvxPSQNMGc

Hoop Shredding Gigolo (pictured above) : https://youtu.be/bpR0bULsl-0&t=787

This is Pat Finnerty’s (accurate) take on writing a hit Offspring song.

Easy Mode: Amish Paradise

Hard Mode: Shia LaBeouf

Maybe a stretch as it’s not parodying a song but parodies Star Wars kinda sorta? Seagulls! (Stop it Now)

Lonely Island has a few (Jack Sparrow) comes to mind but again not a direct parody of a specific song.

Richard Cheese does straight up covers but they are so stylistically different that it’s basically a parody. Chop Suey

Then there’s the classic comedy music duos: Garfunkel & Oates (Loophole), Flight of the Conchords (Business Time)

Bo Burnham’s whole Inside special is fantastic too.

Looks like I’m mostly listing comedy music and not necessarily parodies, but oh well.

Hey it’s pat finnerty big up my dude

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Pachelbel Rant by Rob Paravonian

If its parody songs specifically, then hard mode isn’t possible for me

But if comedy music is allowed, much of Ninja Sex Party is on repeat, as well as a bunch of Tim Minchin’s work

The Ghoul - He got the wrong foot amputated, parody of Come and Play by the Offspring

Bo Burnham’s Kanye Rant