One of Gloomy's suicide attempts
Gloomy hiding away from the fun
Gloomy falls for an old trick
Gloomy seems to have put on extra sunscreen
Gloomy will survive this too
Formerly cheerful Gloomy playing with his ball
A rare and touching sight of Gloomy's smile
Gloomy about to jump from a clock tower.
Gloomy about to take a deadly dip
Oh, Nubby. Can't you learn?
Gloomy and
Drama in a play
Has Gloomy died and gone to heaven?
Gloomy is about to be hit by an asteroid, but he doesn't care
Fan Art By ThatOneNeighbor
Gloomy failing to kill himself
"Hit me with your best shot."
He's smiling on the inside.
Gloomy being reminded of his old ball.
Roger, Crafty and Gloomy. Art by ShiftyKleptomaniac.
Walking in on something they probably should not have...
We love ourselves a short king!
Art by Nectar on Discord.
He manages to survive this, by the way.
This was funnier in my head