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Obama, Barrack
Pictures of President Barrack Obama often find their way into Fark Photoshop contests, especially the iconic blue and red image created by pop artist Shepard Fairey during the 2008 campaign.

Octomom
Nadia Suleman (aka: the Octomom) is a mother of 14 living in California. Her delivery of octuplets drew national attention in 2009. This picture, taken during the late stages of that pregnancy, is an inevitable addition to any Octomom discussion thread on Fark.

Office Space
This is a scene from the 1999 movie "Office Space." I haven't seen the film, so I can't elaborate on the exact circumstances of this scene, but the link has the basic plotline along with a lot of spoilers. It appears infrequently, but often enough to be recognizable as a cliché.

O RLY Owl
The O RLY owl was a Snowy Owl named Jonathan that lived in the San Diego Zoo. The photo was taken by nature photographer John White. The surprised look on the owl's face is a bit humorous and has endeared it to a number of Photoshoppers. Jonathan died of pneumonia in 2006.
Thanks to nightmaretony for the background info.

Oswald, Lee Harvey - See Ruby-Oswald Assassination