head

a head ahead Hall of Fame head homophones horse Horse Racing literalism racing space the headless horseman - 6408940544
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It's kind of a catch-22, really. If you don't bet on the headless horseman, you're probably going to get murdered. If you do bet on the headless horseman, your wallet's probably going to get murdered. CONUNDRUM. - Matty Malaprop

double meaning head literalism pot pothead - 5583636224
By MajorKpopper (Via: Irene Kale)
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... or this is your drugs on a cranium, depending on whether you have predilection for keeping your pot in a pot or not. - Matty Malaprop

alligator gator head investigator investor literalism shoop similar sounding - 5728253696
By rostama
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The change from prospector to inspector isn't the most subtle change I've ever seen... (thanks to Punmaster rostama for the prospector-inspector bit!) - Matty Malaprop

cocking double meaning floating giant head literalism lolwut sandwich - 5540166400
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Surrealiously you guys, that's the only appropriate reaction to such an incident in my mind. - Matty Malaprop

double meaning head literalism pig pigheaded - 6522537216
By xyzpdq1
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And here in one picture we have basically everything I hate about the Internet. I'll let you guys extrapolate from that statement as you wish. - Matty Malaprop

standing head over heels Twist Ending heels head lolwut literalism - 6993988352
Via: We All Draw
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I mean, it was cute I guess, but it wasn't like a corgi or a baby basset hound or anything... - Matty Malaprop