webcomics 20 Comic Strips That Are Hilariously Depressing  

Stephen Reyes
55.2k votes 10.2k voters 590.5k views 20 items

Is there anything more bittersweet than comics that are both funny and sad? They hit you right in that sweet spot that makes you smile and feel like your gut has been punched at the same time. Depressing comics have been a mainstay on the Internet for a long time, and over the years aspiring illustrators have mastered the art form.

Vote up these unbelievably funny and depressing comic strips, particularly the ones that made you laugh and feel terrible at the same time.

1 2,529 VOTES

Promotion


Promotion is listed (or ranked) 1 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  Zach Weinersmith
2,087 442
Is this funny, but sad?
2 2,844 VOTES

College


College is listed (or ranked) 2 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  Yesterdays Popcorn
2,336 508
Is this funny, but sad?
3 2,712 VOTES

Real Treasure


Real Treasure is listed (or ranked) 3 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  It's the Tie/Mr. Lovenstein
2,231 481
Is this funny, but sad?
4 3,246 VOTES

Glad I Found You


Glad I Found You is listed (or ranked) 4 on the list 20 Comic Strips That Are Hilariously Depressing
Photo:  Ryan Hudson
2,654 592
Is this funny, but sad?