The Doug Anthony All Stars as a most liked

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.

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!!!

Flight Of The Conchords

The Smothers Brothers, Tim Minchin, and Tom Lehrer

They had a pretty limited musical run (and a 1 season IFC show) but Garfunkel and Oates had some funny songs

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.

The Arrogant Worms, and Three Dead Trolls in a Baggie. Canada stays winning.

Richard Cheese - a lounge singer doing some fun covers

Jon Lajoie

I've always liked Steel Panther, good hair metal, just rude, crude and funny.

Ninja Sex Party is good value.

Flight of the Conchords are awesome.

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

The Brett Domino Trio

Tripod

Here Come The Mummies.

Victor Borge has always been good for a laugh. Very Looney Tunes.
Piff the Magic Dragon.
Jonathan the Terrible
Tiny Girl Big Show.
Jacques Ze Whipper.

Gallagher isn't my favorite but idk if I've seen enough to say he's a dislike.

Psychostick is probably my favorite. Ice nine kills is my least favorite.

Would the Bloodhound Gang be considered comedy? always loved Bloodhound Gang. sure they had that one song but the CKY videos introduced me to their other stuff which is quite good.

Steve 'N Seagulls, bluegrass covers of metal songs!

Bo Burnham and Steven Lynch

I know this is meant for english speakers, but for francophones folks around here, Ultra Vomit is a great band if you're into metal and dumb jokes (like this song parodying the french Hokuto no Ken opening, talking about (Heine)ken beers).

Tenacious D isn't in this thread yet

Agreed with Weird Al, of course.

Also, Tom Cardy.

This guy might be a one-hit wonder -- I haven't even checked out whatever else he might've done -- but I absolutely love that one video because I also played cello in school.

Jonathan Coulton

Brental Floss (game music with goofy lyrics added) can be fun. A lot of it is profane or not funny though, so it's a mixed bag.

Smooth McGroove (VGM acapella) isn't comedy, but his angle is somewhat of a novelty.

John Kampen is pretty good, and Alice Boersma. I don’t like Jose van der Velde, his lisp gets on my nerves.

Lots of good acts in these threads, I haven’t seen them mentioned so I will throw out Trout Fishing in America.

Let's see... Nerf Herder (whose lead singer is Parry Gripp, famous for Raining Tacos and other songs), Sub-Radio, Rumahoy, and John Trubee (Blind Man's Penis).

I used to be a fan of NanowaR of Steel, but unfortunately they've got some transphobic songs that sour the rest of the band's music for me. That being said, Valhalleluja is a masterpiece and always will be even though Thomas Winkler is in it.

I hate to call them novelty or comedy because they're amazing musicians, but I'd suggest Ween.

Jim E. Brown

He's a young lad from the UK that has a degenerative disease that makes him look old.