Painlarious 

When something happens that is hilariously painful for the person/persons involved.

When Rondo of the Boston Celtics got close-lined by the Miami Heat's Igaulskas dick in the Celtics-Heat game on February 13th, 2011 it was Painlarious.

Painlarious by fanofdirtybball March 1, 2011

pielarious 

hilarious times 3.141592653589793238462643383279502884197169399375105820974944592307816406286208998628034825342117067982148086513282306647093844609550582231725359408128481117450284102701938521105559644622948954930381964428810975665933446128475648233786783165271201909145648566923460348610454326648213393607260249141273724587006606315588174881520920962829254091715364367892590360011330530548820466521384146951941511609

so it is something more funny than hilarious

Dude that was pielarious and awesome

pielarious by Thierry and Oscar June 20, 2011

painfularious 

Something so bad, so awful, it's downright painful but you can't help but laugh at it in misery.

I was on the train and this girl was singing Smash Mouth's All Star on her iPod, and singing it badly... it was so painfularious but I couldn't stop laughing.

painfularious by mdhattar December 28, 2010