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55378008 

Its 'calculator-speak' (type the number in the calculator and turn it upside-down) for the word boobless. Probably the most well known phrase typable in a basic calculator.
Other words include:
5318008 (boobies)
58008 (boobs)
77345 (shell)
710.77345 (shell oil)
318ll345 (shelbie)
7734 (hell
07734 (hello)
Im the coolest person in school person i can type a rude word in my calculator. 55378008
55378008 by Josh Clow April 3, 2007
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55378008 

Wow... lot's of variations I've never heard of. The only way I've ever heard this was with Dolly Parton.

"In nineteen 69 Dolly Partons Doctor said her Tits were 2 2 2 Big. So he gave her 51 Pills to take 8 Times a day, and when she woke up in the morning she became BOOBLESS.
6922251 x 8 = 55378008
55378008 by Biker Scout August 29, 2007

55378008 

I also heard this calculator joke in Third grade from a friend.
A woman had 69(press 69) boobs,
which she was 2(press 2), 2(press 2), 2(press 2) much.
So she went to 51st(press 51) street
to visit DR. X (press multiply)
8(ate) press 8) her boobs and now she's

6922251x8= BOOBLESS
55378008 by sss3d July 16, 2004

55378008 

There was a girl aged 13 who had boob size 84 but she wanted down to 45, so the doctor said 0 take 2 tablets, but instead she took 4 and that left her BOOBLESS
13844502 x 4 = BOOBLESS, motherfucker
55378008 by jimad December 1, 2003

55378008 

when typed into a calculator and flipped upside down it reads "BOOBLESS"
hey jane, you are ....*types into calculator and flips*! HAHAH
55378008 by erica October 24, 2003

55378008 

Type it upside-down in a calculator and it reads "BOOBLESS"
55378008 by Anonymous October 4, 2003