I will update this OP with winners, sort of like our own hollywood walk of fame. Enjoi.
Caption contest 1:
Winner: MotherGunner
Recieved: Virtua Tennis (dreamcast)
Caption contest 2:
Winner: _joshuaTurbo
"The tailgating scene for the upcoming 2013 XFL season!!"Recieved: Jack Nicholas Golf (nes) and Alisia Dragoon (genesis)
Caption contest 3:
Winner: Ji-L87
"Welcome, Mr.Bond. I hope my henchman didn't give you too much trouble?"Recieved: Medal of Honor (gba)
Caption contest 4:
Winner: Necromancer
"In the story of the Tortoise and the Hare, who knew that 'slow' had nothing to do with speed?"Recieved: Wild West Shootout (wii)
Caption contest 5:
Winner: TheClash603
"The old purse handle tit framing technique. Makes even fat chick knockers look delicious."Recieved: Star Soldier (nes)
Caption contest 6:
Winner: _joshuaTurbo
"Do you really think we'll need these to play Camp California?" "f*ck yeah we do!!"Recieved: Hardcore 4x4 (saturn)
Caption contest 7 (guess that 'stache):
Winner: esteban
Crushed it quickly.
Recieved: Shooter - Space Shot (ps1)
Caption contest 8 (guess that 'stache):
Winner: Jibbajaba
Recieved: FORFEIT
Caption contest 9:
Winner: TheClash603
"Victoria Secret filed for bankruptcy today. Company management said the new direction of the angels didn't resonate with the buyers."Recieved: Bomberman (gameboy)
Caption contest 10:
Winner: Opethian
"meanwhile in Detroit..."Recieved: Dragon Slayer (PCE)
Caption contest 11:
Winner: roflmao
"Upon hearing the news of another Ant Invasion, Greg Bradley heads back to the desert."Recieved: Zero 4 Champ II (PCE)
Caption contest 12:
Winner: nullity
"Bill had learned his lesson after losing the tips of all four fingers; this time, he used a fork."Recieved: Spy Hunter (3DS)
Caption contest 13:
Winner: _joshuaTurbo
"Soop, for the last time- NO you cannot take Donna home!"Recieved: Guardian Legend (NES)
Caption contest 14:
Winner: Arkhan
"who the f*ck let Justin Bieber in. "Recieved: Prince of Persia (PS2)
Caption contest 15:
Winner: InfraMan
"CeeLo Green, before he harnessed the power of OBEY!"Recieved: I don't remember what I sent (PCE)
Caption contest 16:
Winner: TheOldMan (passed the win to nullity)
TheOldMan: "Honestly. Howard meant nothing to me..."nullity: ""Smell my fingers..." Galam whispered seductively."Recieved: MechWarrior 2 and Missle Command(PS1)
Caption contest 17:
Winner: TheClash603
I never thought I was a racist until I tried to come up with a caption for this picture. You've made me ashamed of myself.Recieved: Forgotten Worlds (genesis)
Caption contest 18:
Winner: Opethian
"AY ANYONE GOT DA WIFI PASSWORD SO I CAN PLAY MADDEN"Recieved: Sengoku Mahjong and Naxat Stadium (PCE)
Caption contest 19:
Winner: xelement5x
"Tom realized to late that he had misheard his friends when they told him to "Do her in the bucket"."Recieved: Dementia 13 (DVD)
Caption contest 20:
Winner: nullity
"Swipe right"Recieved: Alzadick (PCE)
Caption contest 21:
Winner: esteban
Recieved: Golden Sun (DS)
Caption contest 22:
Winner: esteban
Beats by Zune.Recieved: Camp California Soundtrack
Caption contest 23:
Winner: xelement5xnullity didn't realize that taking just one gerbil out of the wheel for a little "me" time would totally cut the power to his webseverRecieved: Sherlock Holmes CD w/ newspapers
Caption contest 24:
Winner: BlueBMWSoop: 1 year after DonnaRecieved: Super Mario Maker (Wii U)
Caption contest 25:
Winner: geiseHello? Yes...we do VGA grading.Recieved: Surprise