Any recommendations?

[sengir]

Sullivan's Travels
Scarecrow
Bound For Glory
The Grapes Of Wrath
Death Of A Salesman
Salesman (documentary)

Life Stinks by Mel Brooks even...

[cagedwisdom]

Salesman (documentary)

Was about to mention this, definitely worth checking out.

[sengir]

Another two

Glengarry Glen Ross
Slasher (docu)

[paulofilmo]

Exils - The IMDb keyword list reads like a wonderful gypsy fairytale.
Into The Wild

Charlie Chaplin movies

Look out for films about outlawed cowboys (Westerns generally), mountain men, gypsies, losers, immigrants, peripatetic tribes, ethnographic studies..

The relevance of everything after the line is arguable/tangential/tenuous.
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Bold=better fits the brief

I love the Magic Lantern guy at the beginning of Comrades.

O Lucky Man! - does pretty much everything in one way or another

The Man Who Would Be King - an adventure, but they always feel like drifters to me


Then there's the war-torn/dystopia/prison camp/almost getting by in interesting ways type films. ala:
Grave of the Fireflies
Turtles Can Fly
Import/Export
Midnight Cowboy
The Man Without a Past
A Generation (1955)
Nobody Knows (2004)
King Rat
Sansho the Bailiff - maybe. ages since I saw this
Oliver Twist - juxtaposes class. pickpocketing orphans
The Plague Dogs
I Don't Want to Sleep Alone
(there's obv. millions more of these)

Films where it feels like the lead could up and leave at any time (generally without 'roots' or 'foundation'):
Boys Don't Cry
Kiki's Delivery Service
2046
Ghosts
The Horseman on the Roof
Man Who Plants Trees
The Magician / Sawdust & Tinsel
Chinatown
Buffalo '66
Zatoichi
The Unloved (2009)
Three Colors: Blue
Terminator movies
Running on Empty
Anything by the Dardenne brothers
Pitch Black
Following (1998) - a thief
The Dreamlife of Angels (the lead begins a homeless peddler)
Brysomme mannen, Den
Pyaasa (1957)
Jeremiah Johnson
Alice in den Städten
Alice Doesn't Live Here Anymore
Catch Me If You Can
Princess Mononoke
The Plague Dogs
Rumble Fish
Days of Heaven
3-Iron
The Three Burials of Melqui…
The Godless Girl
Le Conseguenze dell'amore
Chungking Express
Withnail & I
The Return
Hallam Foe
Badlands
Crouching Tiger, Hidden Dra…
Roger Dodger
Harold and Maude
Naked

You might also like the con/grifter films; like Nine Queens.

[tef]

Or "The Grifters."

[theficionado]

I wasn't terribly enthusiastic about it, but Wendy and Lucy certainly fits the bill.

[Stewball]

Best Hobo movie ever, Emperor of the North, where A#1, champeen Bo (Lee Marvin--see below & above) takes on the railroad bull, Shack (Earnest Borgnine), to ride his train to the end of the line, with Cigarette (Keith Carradine) playing both sides against the middle. Great story, acting, scenery and even music if you ignore the lyrics during the opening credits.



As for a wanderer flick, how can you beat a movie based (loosely on the Odyssey) with outstanding music, characters and one of the most off beat stories ever. That, of course, would be O Brother, Where Art Thou?

Traveling Salesman, Professor Howard Hill, The Music Man, who gets his foot caught in the door. If you don't like musicals in the traditional sense, skip it. But if you do, you've almost certainly seen it already anyway.

[MmzHrrdb]

Into the Wild is right up that alley.