Movies Like Bootleg Wisconsin

If you liked Bootleg Wisconsin (2008), a movie directed by Brandon Linden, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Son of Rambow (2007)
★ 6.7/10
Will is looking for an escape from his family when he encounters Lee, the school bully. Armed with a video camera and a copy of Rambo, Lee plans to make his own action-packed video epic.
2
Stargirl (2020)
★ 7.4/10
An unassuming high schooler finds himself inexplicably drawn to the free-spirited new girl, whose unconventional ways change how they see themselves…and their world.
3
Lucas (1986)
★ 6.7/10
A brilliant but socially inept 14-year-old experiences heartbreak for the first time when his two best friends – Cappie, an older-brother figure, and Maggie, the new girl with whom he is in love – fall for each other.
4
12 Gifts of Christmas (2015)
★ 6.1/10
When Anna Parisi, an unemployed fine arts painter, is unable to make ends meet, she is hired to become a personal Christmas shopper for Marc, an uptight corporate exec. As they begin working together, Marc learns that…
5
One Starry Christmas (2014)
★ 6.5/10
An aspiring astronomy professor finds unexpected Christmas romance when she meets a charming cowboy during her holiday travel. As she decides between this new cowboy and her practical boyfriend, she must decide whether…
6
Rip Girls (2000)
★ 6.3/10
A teen-age girl and her father come to an island on Hawaii, they find a closer relationship to each other and think about changing the island. During her adventures, Sydney finds friends, a new hobby with her fantastic…
7
John Tucker Must Die (2006)
★ 6.1/10
After discovering they are all dating the same same guy, three popular students from different cliques band together for revenge, so they enlist the help of a new gal in town and conspire to break the jerk's heart…
8
Falling in Love (1984)
★ 6.6/10
During shopping for Christmas, Frank and Molly run into each other. This fleeting short moment will start to change their lives, when they recognize each other months later in the train home and have a good time…
9
An Autumn Romance (2021)
★ 7/10
When librarian Taylor Harris suddenly loses her job, she decides to visit her brother in a small town in Montana. There, she gets involved in the fight to help save her brother's hotel from tycoon Joel Sheenan, who…
10
A Woman of Paris: A Drama of Fate (1923)
★ 6.7/10
When Marie St. Clair believes she has been jilted by her artist fiance Jean, she decides to leave for Paris on her own. After spending a year in the city as a mistress of the wealthy Pierre Revel, she is reunited with…
11
Larry Crowne (2011)
★ 6/10
When he suddenly finds himself without his long-standing blue-collar job, Larry Crowne enrolls at his local college to start over. There, he becomes part of an eclectic community of students and develops a crush on his…
12
Geek Charming (2011)
★ 6.7/10
Film geek Josh is looking for the subject of his new documentary when a chance meeting puts the perfect star in his sights—Dylan, his school's most popular junior. But Dylan's hopes of using the film to become Blossom…
13
The Rewrite (2014)
★ 6/10
An Oscar-winning writer in a slump leaves Hollywood to teach screenwriting at a college on the East Coast, where he falls for a single mom taking classes there.
14
Christmas Wonderland (2018)
★ 6/10
Heidi, who initially left her small town of Pleasant Valley with the dream of one day becoming a successful painter, has put her own art on hold to excel as an art gallery curator. Now, a week before the gallery’s big…
15
Head Full of Honey (2018)
★ 6.4/10
A young girl tries to help her grandfather, who is suffering from Alzheimer’s, navigate his increasing forgetfulness, and ends up going on a remarkable adventure with him.
16
Lovely, Still (2009)
★ 6.6/10
A holiday fable that tells the story of an elderly man discovering love for the first time.
17
A Christmas Melody (2015)
★ 6/10
Kristin has just had to close her small Manhattan clothing boutique to return to her Ohio home town and live in her parents' former home. It's an adjustment for Kristin and her young daughter— especially when she runs…
18
Good Luck Charlie, It's Christmas! (2011)
★ 6.7/10
Teddy Duncan's middle-class family embarks on a road trip from their home in Denver to visit Mrs. Duncans Parents, the Blankenhoopers, in Palm Springs. When they find themselves stranded between Denver and Utah, they…
19
Uptown Girls (2003)
★ 7.1/10
Molly Gunn, the freewheeling daughter of a deceased rock legend, is forced to get a job when her manager steals her money. As nanny to Ray - the precocious, oft-ignored daughter of a music executive - she learns what…
20
Merry Christmas, Drake & Josh (2008)
★ 7.3/10
Step brothers Drake and Josh must give a foster family the best Christmas ever or face years in jail for a Christmas party gone wrong.