Most Similar Movies to Lonesome Jim (2005)
If you are looking for movies like Lonesome Jim (2005), you might like movies tagged with keyword : independent film, drama, black comedy, family, coming of age, small town life, depression, self-discovery, loser, unemployment, family bonds, life struggles, realism, interpersonal relationships, lost, social pressure, loneliness, humor, failure, psychological struggle .
What's Eating Gilbert Grape (1993), Pranzo di Ferragosto (2008), Trees Lounge (1996), Judy Berlin (1999), Lovely & Amazing (2001), Jeune femme (2017), The Weather Man (2005) ... Let's take a look at the following list...

What's Eating Gilbert Grape (1993)
After his father's death, Gilbert has to care for his mentally-disabled brother, Arnie, and his morbidly obese mother. This situation is suddenly challenged though, when love unexpectedly walks into his life.
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Pranzo di Ferragosto (2008)
In order to work off a debt, a man (Gianni Di Gregorio) takes care of four elderly women during an important Italian holiday.
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Trees Lounge (1996)
Tommy is an unemployed mechanic who spends most of his time in a bar (Trees Lounge) in a small blue collar town. He seems to always be thinking, "If only X then I could stop drinking".
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Judy Berlin (1999)
A lonely, but talented teacher enjoys a flirtation with the (married) principal of the school, who returns her affections, but is hampered by his family members. Whilst the teacher and principal can steal their fleeting moments during an eclipse.
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Lovely & Amazing (2001)
Self-esteem and insecurity are at the heart of this comedy about the relationship between a mother and her three confused daughters.
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Jeune femme (2017)
Left by Joachim, an artist with whom she shared her life for 10 years, Paula finds herself wandering the streets of Paris, lonely and fixated.
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The Weather Man (2005)
A Chicago weather man, separated from his wife and children, debates whether professional and personal success are mutually exclusive.
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Just Before I Go (2014)
On the verge of giving up on life, a guy travels to his hometown to make amends.
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Looking for Kitty (2004)
A high school baseball coach (Krumholtz) and a down-on-his-luck private investigator (Burns) form a bond as they scour New York City for the coach's wife, who's run away with a second-rate rock star. As in Burns' previous films, the city itself becomes a character as the two men confront their fear of change and the familiar habit of loneliness.
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Funny Ha Ha (2003)
After graduating from college, Marnie (Kate Dollenmayer) is living in Boston. Looking for temporary work while trying to figure out what it is she wants to do, Marnie grapples with her feelings toward her good friend Alex (Christian Rudder), who doesn't seem to feel the same way about her. As she attempts to mature while surviving her dreary desk job, Marnie meets Mitchell (Andrew Bujalski), a shy, neurotic coworker who helps her better understand herself.
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Look at Me (2004)
A gifted singer (Marilou Berry) seeks approval from her egotistical father (Jean-Pierre Bacri), who is a famous writer and publisher.
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Tiny Furniture (2010)
After breaking up with her boyfriend, a recent college graduate (Lena Dunham) moves back in with family while she tries to figure out the next step in life.
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Three Quarter Moon (2011)
6-year old Hayat turns up in Hartmut's taxi without a word of German. All attempts to get rid of her fail. So he resigns himself to helping her find her mother. But is he helping her or she helping him? Slowly Hayat changes his outlook on life.
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Paris (2008)
A ex-dancer has a heart problem and even with a transplant, he may still only have a few months to live. Time's spent looking at people/life in Paris from his balcony. His single mom sister moves in with her 3 kids to look after him.
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Big Fan (2009)
A hard-core New York Giants fan struggles to deal with the consequences when he is beaten up by his favorite player.
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Grandma (2015)
A teenager facing an unplanned pregnancy seeks help from her acerbic grandmother, a woman who is long estranged from her daughter.
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Citizen Duane (2006)
A high-school student (Douglas Smith) seeks to restore his father's honor by toppling the man's nemesis, the longtime mayor of their small town.
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Rocket Science (2007)
Looking for answers to life's big questions, a stuttering boy joins his high school debate team.
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