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9 Famous Tween Hobos

In honor of the publication of Tween Hobo: Off the Rails, we take a look at some of our favorite hobos throughout history.

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1. Natty Gann

Natty Gann (played by Meredith Salenger) is the 12-year-old protagonist of Disney’s 1985 kid-adventure flick, The Journey of Natty Gann. Set during the Great Depression, the film tells the story of a tomboyish girl who escapes from a boardinghouse and hits the road in search of her father, who has gone to look for work as a logger in the Pacific Northwest. Along the way, she befriends a wolf and has an “innocent romance” with a young John Cusack.

2. Huckleberry Finn


Mark Twain’s seminal contribution to the Tween Hobo genre, Huck Finn is Tom Sawyer’s “lawless and vulgar” best bud, son of the town drunk, friend and traveling companion to runaway slave Jim. According to no less than Ernest Hemingway, “All modern American literature comes from one book … called Huckleberry Finn.”

3. Young “Woody” in Bob Dylan biopic I’m Not There


In Todd Haynes’s experimental Bob Dylan biopic I’m Not There, the legendary folksinger is played by six different actors, including Cate Blanchett, Heath Ledger, Christian Bale, and this kid – Marcus Carl Franklin. Franklin’s tween hobo personification of a young Dylan-meets-Guthrie rides the rails with a guitar case bearing the slogan, “This Machine Kills Fascists.”

4. Mary-Kate Olsen


Sometimes you have to be rich to look this poor. Mary-Kate Olsen, the uber-tween and kajillionaire of Full House fame, graduated to full-scale fashion icon with her introduction of “hobo chic” in the mid-aughts. Long, raggedy scarves; street-sweeping jackets and cardigans with holes in them; the messier and baggier the better. These days Mary-Kate tends to rock a sleeker look, but let’s be honest – she never looked as good as when she looked like she had just crawled out of a dumpster.

5. The Boxcar Children


The prototypical tween hobos just might be the four orphan stars of this classic children’s series, written by first-grade teacher Gertrude Chandler Warren. Henry, Jessie, Violet and Bennie make a parent-less home for themselves in an abandoned boxcar, and embark on a fruitful career as amateur sleuths, solving well over a hundred mysteries, including the caboose-related one featured here.

6. Addie Loggins in Paper Moon


In 1973’s Depression-set comedy Paper Moon, Tatum O’Neal gives a legendary performance as 9-year-old Addie Loggins, who may or may not be the daughter of con man Moses Pray, played by Tatum’s real-life father, Ryan O’Neal. Addie and Moze join forces and scam their way across America, on a road trip full of hillbillies, bootleggers, gold-diggers, and carnival barkers. Nine-year-olds really shouldn’t smoke, but Addie Loggins makes it look cool.

7. Oliver Twist


Another crucial figure in the pantheon of child criminals, Charles Dickens’s orphan-turned-pickpocket Oliver Twist is depicted on the French book cover above with a classic hobo’s bindle.