Caption This
Posted on April 29th, 2013 - By Bossip Staff
Categories: Caption This, Elsewhere In The World, News, Originals, What is Wrong With This Picture, What the Hell???

OUCH!! Continue »
Posted on April 29th, 2013 - By Bossip Staff
Categories: Caption This, Elsewhere In The World, News, Originals, What is Wrong With This Picture, What the Hell???

OUCH!! Continue »
Posted on April 13th, 2013 - By Bossip Staff
Categories: Ballers, Caption This, Gay, News, Old Heads, out of pocket, Pure Comedy, SMH, What the Hell???

Uhhhh, sir…? Continue »
Posted on March 19th, 2013 - By Bossip Staff
Categories: News, Originals, Pure Comedy, SMH, What the Hell???
Posted on February 18th, 2013 - By Bossip Staff
Categories: Ballers, Caption This, News, Pure Comedy, Question Characters, SMH, What the Hell???

Folks just can’t let Chrissy Bosh be great Continue »
Posted on February 14th, 2013 - By Bossip Staff
Categories: Barack Obama, Bolitics, Caption This, For the Children, News, What the Hell???

Why you over there lookin’ at me…? Continue »
Posted on December 27th, 2012 - By Bossip Staff
Categories: Caption This, News, Originals, Pure Comedy

Best. Santa. Picture. Ever. Continue »
Posted on November 23rd, 2012 - By Bossip Staff
Categories: Caption This, Hate It or Love It?!?!, News, What the Hell???

Would you let your dog do this?
Continue »
Posted on November 19th, 2012 - By Bossip Staff
Categories: Are You Feelin This Get Up?, Caption This, Dude-Where is My Stylist?, News, Random Ridiculousness
Posted on November 17th, 2012 - By Bossip Staff
Categories: A "Lil Positivity", Caption This, Congratulations, For Your Information, News, On the Come up, Recession Is Real, Rumor Control, What You Know About It?
Posted on November 13th, 2012 - By Bossip Staff
Categories: Ballers, Bangers, Caption This, Gay, News, Pure Comedy, SMH, Suspect, What the Hell???

Say bruh… Continue »
Posted on November 9th, 2012 - By Bossip Staff
Categories: Bolitics, Caption This, Did You Know, For Your Information, News, Sh*t Is Real, Yeah We Said It
Posted on November 7th, 2012 - By Bossip Staff
Categories: Barack Obama, Bolitics, Caption This, celeb, ChitChatter, Did You Know, Elsewhere In The World, For Discussion, For Your Information, Hate It or Love It?!?!, Michelle Obama, News, out of pocket, Put on Blast, Race Matters, SMH, The Side-eye, What Were You Thinking?
Posted on October 4th, 2012 - By Bossip Staff
Categories: Bangers, Bolitics, Caption This, Freaks, In White Folks News, News, Perverts, Pure Comedy, SMH

Great googly-moogly them thangs is juicy! Continue »
Posted on October 2nd, 2012 - By Bossip Staff
Categories: Caption This, Elsewhere In The World, Hate It or Love It?!?!, Jennifer Lopez, Kanye West, Multi, News, Out and About, Seen on the Scene, SMH, Spotted

Say Ye’, say Ye’ don’t you look ghey every day-day?? Continue »