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1.
a hobo is an itinerant worker, a career which sprang up during the depression. A hobo, unlike a bum or a tramp, is more than willing to work, but mostly for a short duration, as their main impetus is travel, the love of the journey above the actual destination. A bum is stationary, feeding off of those unfortunate enough to cross his path; a hobo merely travels from town to town, finding work when he can, but only for the sake of financing his next adventure. NEVER call a hobo a bum...they'll kick your sorry no-bo ass!
"When I first started hobo'in,
I took a freight train to be my friend
-John Lee Hooker
by hoboerotic August 12, 2004
 
2.
Hobos are a peaceful people.Being homeless and pennyless, similar to MC Hammer. They go place to place taking money from people for doing odd jobs, whether it be pulling weeds, kiiling roaches, cleaning roach poop, or eating roaches.

They're like uh...drifters. Telling stories to whoever they can
Boy: Grandpa! What are those carving symbols?

Grandpa: You see here son, these be hobo signs! This here sign means, there's work for cornbread 2 blocks up.
Hobos LOVE cornbread...
by Christopher Ess July 17, 2005
 
3.
A free man/woman who is no longer trapped in the society of capitalism and time. He/she can go to sleep whenever he/she wants to, and do anything.
Hobos are good at recycling dumpstered food that huge coporations throws out.
That hobo just found a whole bag of pies in our dumpster!
by Exorph May 26, 2004
 
4.
the most kickass people in the world, also the coolest job in the world.

someone who could do something with their lives but don't want to.
I would rather be a hobo
by matt dold January 15, 2004
 
5.
ho·bo
noun
One who wanders from place to place without a permanent home or a means of livelihood.

adjective
Hip n groovy

verb
To do as a hobo does; the act of sitting in random areas for no good reason.
That hobo is too hobo to be hobo. Yes.
by Timmylicious April 16, 2007
 
6.
1. Originally referred to poor, homeless itinerant workers in the USA. These original hobos travelled from town to town seeking temporary employment, usually along the lines of physical labour. They are traditionally associated with freighthopping (illegally riding in the carriages of freight trains). See also drifter, vagabond and okie.

2. Nowadays commonly used throughout the English-speaking world to refer to any homeless person. See also bum, tramp and beggar.
Traditional hobos are often romanticized in popular culture, for example in the books "Of Mice and Men" by John Steinbeck and "On the Road" by Jack Kerouac and in the music of Woody Guthrie.

The portrayal of modern homeless people, however, is usually much less favourable, with a widespread belief that homelessness is self-inflicted and that these "bums" should "just get jobs".
by backpacker_x2 February 15, 2011
 
7.
A tight ass clothing line originated in Washington D.C

named H.O.B.O meaning Help Our Brothers Out.

Only worn by blacks and fake white people.

Thats why its help our BROTHERS out
Me: Im goin to the H.O.B.O shop to get some new shit
Friend: iight son hit me up later
by Da_Youngest_In_Charge January 20, 2006