Most Similar Movies to Gaily, Gaily (1969)
If you are looking for movies like Gaily, Gaily (1969), you might like movies tagged with keyword : runaway, madam, prostitute, editor, friend, reporter, amusing, endearing, inspiring, spirited, chicago, brothel, newsroom, small town, coming of age, unlikely allies, friendship, politics, corruption, journalism, growing up, discovery, quest, love, 1910s .
Playing It Cool (2014), Summer Night (2019), Then Came You (2018), Late Night (2019), The Brothers (2001), A Bad Idea Gone Wrong (2017), Duck Duck Goose (2018) ... Let's take a look at the following list...

Playing It Cool (2014)
Unrequited love motivates a guy to write about his experiences.
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Summer Night (2019)
A coming-of-age story about the complexities of young romantic relationships.
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Then Came You (2018)
A hypochondriac working as an airport baggage handler is forced to confront his fears when a British teenager with a terminal illness enlists him to help her carry out her eccentric bucket list.
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Late Night (2019)
A late night talk show host suspects that she may soon lose her long-running show.
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The Brothers (2001)
Four friends (Morris Chestnut, D.L. Hughley, Bill Bellamy) question women, relationships and honesty after one of them becomes engaged.
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A Bad Idea Gone Wrong (2017)
Two would-be thieves forge a surprising relationship with an unexpected house-sitter when they accidentally trap themselves in a house they just broke into.
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Duck Duck Goose (2018)
A bachelor goose must form a bond with two lost ducklings as they journey south.
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The Hot Chick (2002)
An attractive and popular teenager, who is mean-spirited toward others, finds herself in the body of an older man, and must find a way to get back to her original body.
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Brother Bear 2 (2006)
A bear (Patrick Dempsey) helps a childhood friend (Mandy Moore) travel through the wilderness to burn a powerful amulet.
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The Bachelor (1999)
A commitment-phobic man goes in search of a bride, including his fed-up girlfriend, to inherit his grandfather's $100 million inheritance.
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Isle of Dogs (2018)
Set in Japan, Isle of Dogs follows a boy's odyssey in search of his lost dog.
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The Front Page (1974)
A ruthless editor tries to get his top reporter to cover one more crime story before retirement.
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Christmas in the Heartland (2017)
Two teens strike up a friendship while flying to the same small town to spend Christmas with relatives they've never met. They soon agree to switch places and spend the holiday with each other's respective family.
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Cemetery Junction (2010)
A 1970s-set comedy centered on three young working class friends in a dreary suburb of Reading.
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A Shaun the Sheep Movie: Farmageddon (2019)
When an alien with amazing powers crash-lands near Mossy Bottom Farm, Shaun the Sheep goes on a mission to shepherd the intergalactic visitor home before a sinister organization can capture her.
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Hera Pheri (1975)
Two friends Ajay and Vijay gets separated from each other when they discover secrets about their past in their own ways.
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Andy Hardy's Double Life (1942)
All set to graduate from high school and Andy flunks his English exam - in spite of the fact that the Judge has gone to all the trouble of getting him his very own private secretary.
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