Movies Like Sincerely, Willis Wade

If you liked Sincerely, Willis Wade (1956), a movie directed by Vincent J. Donehue, 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
The Million Pound Note (1954)
★ 7/10
An impoverished American sailor is fortunate enough to be passing the house of two rich gentlemen who have conceived the crazy idea of distributing a note worth one million pounds. The sailor finds that whenever he…
2
Great Expectations (2012)
★ 6.4/10
Orphan Pip discovers through lawyer Mr. Jaggers that a mysterious benefactor wishes to ensure that he becomes a gentleman. Reunited with his childhood patron, Miss Havisham, and his first love, the beautiful but…
3
Hardball (2001)
★ 6.5/10
An aimless young man who is scalping tickets, gambling and drinking, agrees to coach a Little League team from the Cabrini Green housing project in Chicago as a condition of getting a loan from a friend.
4
The Big Short (2015)
★ 7.4/10
The men who made millions from a global economic meltdown.
5
Jobs (2013)
★ 6.1/10
The story of Steve Jobs' ascension from college dropout into one of the most revered creative entrepreneurs of the 20th century.
6
X+Y (2015)
★ 6.7/10
Struggling to connect with those around him, a teenage math prodigy trains for the International Mathematical Olympiad, where a budding romance with a fellow contestant breaks through his emotional walls and teaches…
7
Nanny McPhee (2005)
★ 6.7/10
Widower Cedric Brown hires Nanny McPhee to care for his seven rambunctious children, who have chased away all previous nannies. Taunted by Simon and his siblings, Nanny McPhee uses mystical powers to instill…
8
Paycheck (2003)
★ 6.2/10
Michael Jennings is a genius who's hired – and paid handsomely – by high-tech firms to work on highly sensitive projects, after which his short-term memory is erased so he's incapable of breaching security. But at the…
9
Fast Girls (2012)
★ 6/10
A street smart runner develops an intense rivalry with an equally ambitious wealthy young athlete.
10
Old Boys (2018)
★ 6.6/10
In the school-set re-working of Cyrano, an awkward but imaginative pupil helps the handsome but spectacularly dim school-hero pursue the fiery daughter of a visiting French teacher.
11
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.
12
Breathe (2017)
★ 7.4/10
Based on the true story of Robin, a handsome, brilliant and adventurous man whose life takes a dramatic turn when polio leaves him paralyzed.
13
What a Way to Go! (1964)
★ 7.1/10
A four-time widow discusses her four marriages, in which all of her husbands became incredibly rich and died prematurely because of their drive to be rich.
14
Back to School (1986)
★ 6.3/10
Self-made millionaire Thornton Melon decides to get a better education and enrolls at his son Jason's college. While Jason tries to fit in with his fellow students, Thornton struggles to gain his son's respect, giving…
15
The Thinning (2016)
★ 6.6/10
In a post-apocalyptic future where population control is dictated by a high-school aptitude test, two students discover the test is smoke and mirrors hiding a larger conspiracy.
16
Overboard (1987)
★ 6.9/10
Heiress Joanna Stayton hires carpenter Dean Proffitt to build a closet on her yacht—and refuses to pay him for the project when it's done. But after Joanna accidentally falls overboard and loses her memory, Dean sees…
17
You Can't Take It with You (1938)
★ 7.5/10
Alice, the only relatively normal member of the eccentric Sycamore family, falls in love with Tony Kirby, but his wealthy banker father and snobbish mother strongly disapprove of the match. When the Kirbys are invited…
18
Rad (1986)
★ 6.5/10
A BMX racer, who lives in a small town with his mother and sister, is faced with a tough decision, qualify for Helltrack or take his SATs in order to attend college.
19
The Wonderful Story of Henry Sugar (2023)
★ 7.3/10
A rich man learns about a guru who can see without using his eyes. He sets out to master the skill in order to cheat at gambling.
20
Words on Bathroom Walls (2020)
★ 7.8/10
Diagnosed with a mental illness halfway through his senior year of high school, a witty, introspective teen struggles to keep it a secret while falling in love with a brilliant classmate who inspires him to open his…