Movies Like Eddie and the Aviator

If you liked Eddie and the Aviator (2015), a movie directed by Sean Whitesell, 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
Into the Night (1985)
★ 6.5/10
Ed Okin used to have a boring life. He used to have trouble getting to sleep. Then one night, he met Diana. Now, Ed's having trouble staying alive.
2
50 First Dates (2004)
★ 6.9/10
Henry is a player skilled at seducing women. But when this veterinarian meets Lucy, a girl with a quirky problem when it comes to total recall, he realizes it's possible to fall in love all over again…and again, and…
3
Box of Moonlight (1996)
★ 6.8/10
Al Fountain, a middle-aged electrical engineer, is on the verge of a mid-life crisis, when he decides to take his time coming home from a business trip, rents a car, and heads out looking for a lake he remembers from…
4
Always (1989)
★ 6.2/10
The spirit of a recently deceased expert pilot mentors a newer pilot while watching him fall in love with the girlfriend that he left behind.
5
Burke & Hare (2010)
★ 6.1/10
Two 19th-century opportunists become serial killers so that they can maintain their profitable business supplying cadavers to an anatomist.
6
Airplane! (1980)
★ 7.3/10
An ex-fighter pilot is forced to take over the controls of an airliner when the flight crew succumbs to food poisoning.
7
Starman (1984)
★ 6.9/10
When an alien takes the form of a young widow's husband and asks her to drive him from Wisconsin to Arizona, the government tries to stop them.
8
Seeking a Friend for the End of the World (2012)
★ 6.6/10
As an asteroid nears Earth, a man finds himself alone after his wife leaves in a panic. He decides to take a road trip to reunite with his high school sweetheart. Accompanying him is a neighbor who inadvertently puts a…
9
Tin Cup (1996)
★ 6.1/10
A washed up golf pro working at a driving range tries to qualify for the US Open in order to win the heart of his succesful rival's girlfriend.
10
Blue Lagoon: The Awakening (2012)
★ 6.4/10
Two high school students become stranded on a tropical island and must rely on each other for survival. They learn more about themselves and each other while falling in love.
11
Hot Shots! (1991)
★ 6.6/10
The gang that created Airplane! and The Naked Gun sets its sights on Top Gun in this spoof. Topper Harley is a talented but unstable fighter pilot with an axe to grind: clearing the family name. His mission is to…
12
Michael Jackson's Thriller (1983)
★ 8.3/10
A night at the movies turns terrifying when Michael and his date are attacked by zombies.
13
The Greatest Game Ever Played (2005)
★ 7.3/10
A biopic of 20-year-old Francis Ouimet who defeated his golfing idol and 1900 US Open Champion, Harry Vardon.
14
After.Life (2009)
★ 6.3/10
Following a terrible car crash, a woman awakes to find an enigmatic mortician preparing her for burial.
15
The Color of Money (1986)
★ 6.9/10
Former pool hustler "Fast Eddie" Felson decides he wants to return to the game by taking a pupil. He meets talented but green Vincent Lauria and proposes a partnership. As they tour pool halls, Eddie teaches Vincent…
16
The Other Side of the Wind (2018)
★ 6.7/10
At a media-swamped party to celebrate his seventieth birthday and screen his avant-garde film-in-progress, a legendary but jaded Hollywood director is faced both with voracious fans and unsettling questions about what…
17
The Rose Tattoo (1955)
★ 6.9/10
A grieving widow embarks on a new romance when she discovers her late husband had been cheating on her.
18
The Legend of Bagger Vance (2000)
★ 6.6/10
World War I has left golfer Rannulph Junuh a poker-playing alcoholic, his perfect swing gone. Now, however, he needs to get it back to play in a tournament to save the financially ravaged golf course of a long-ago…
19
Perfect Day (1929)
★ 7/10
Two families embark on a pleasant Sunday picnic but manage to run into a variety of issues with their temperamental automobile. Each incident requires repeated exits and reboardings by Laurel, Hardy, their wives and…
20
High Anxiety (1977)
★ 6.4/10
A psychiatrist with intense acrophobia (fear of heights) goes to work for a mental institution run by doctors who appear to be crazier than their patients, and have secrets that they are willing to commit murder to keep.