Here's my personal list of Best Movies about Hoosiers, staring Hoosiers,  or written or directed by Hoosiers.

1. Hoosiers (1987)  What else?   The classic story of small town Hickory and it's basketball team winning the state championship against all odds.  Gene Hackman, Barbara Hershey and Dennis Hopper (in an Oscar-nominated performance) star, but it is the script written by Bloomington native Angelo Pizzo and direction by Decatur, Indiana native David Anspaugh, both I.U. graduates, that captures 1950's small town Indiana, which makes this movie special.  Based closely on Milan's win over perennial power Muncie Central in the 1954 state championship game.  Named  Best Sports Movie by ESPN.  Note: I'm in this one -- as a crowd extra at Hinkle Fieldhouse.
2. A Christmas Story (1983).  This best of all Christmas movies.  It follows 9-year-old Ralphie's quest for the ultimate Christmas present -- a Daisy Red Rider bb gun.  It is full of classic moments -- "double dare you" etiquette, tongue on the frozen flag pole, a culinary review of soap, the Bumpuses hounds, and Chinese turkey.  The movie was written and narrated by Hammond native Jean Shepherd, who just like "Ralphie", grew up on Cleveland Street in Hammond.  The movie is based on the humorist's best-selling books, among them:   "In God We Trust, All Others Pay Cash,"  "Wanda Hickey's Night of Golden Memories and Other Disasters," and "A Fistful of Fig Newtons." 
3. Rebel Without A Cause (1955)  No star ever shined brighter -- or more briefly -- than Fairmount, Indiana's James Dean.  Dean IS a rebel without a cause in this classic movie.  Fifty years later, it still stands as a great movie about the conflicts and pressures of being a teenager.  Dean made only three movies -- East of Eden and Giant (released posthumously) were the others) -- before being killed in a traffic accident on September 30, 1955 while driving in his Porshe Roadster.  The James Dean Museum, Gallery and Festival are all located in Fairmount, where Dean is buried.
4. De-Lovely (2004).  Set in Paris, New York and Los Angeles, this is a musical telling of the life of perhaps America's greatest song writer, who deals with his dedicated wife and homosexual lovers while mesmerizing pre-World War II America with his songs. So what does this have to do with Indiana?  The songwriter is Peru's own Cole Porter, who is played flawlessly by Kevin Kline, an Indiana University graduate.  Ashley Judd gives one of her best performances as Porter's wife, who understands him far better than the rest of the world.  Porter's music is as beautiful as ever, and as the story unfolds, we see the lyrics as something different than what we have always thought.  Overlooked at the box office, this is an imaginative, well-crafted, truly outstanding movie. 
5. Breaking Away (1979) -- Delightful movie set around the annual Little 500 bike race at Indiana University and the conflict between the college students and the "cutters" --  named for the stone cutters who worked the limestone quarries in and around Bloomington.  Dennis Christopher seek plays a local teenager seeking to be something else.  He is so smitten with Italian bike racers that he speaks with an Italian accent, shaves his legs, and pretends to be an Italian to woo a college girl.  Great scenes of Indiana country side and the Little 500 , but the most poignant scene is when the Dad, played by Paul Dooley, walks with his son among the limestone buildings on the I.U. campus.  He explains about being a "cutter" --  how he took pride in his work cutting the stone -- but when the stone became beautiful campus buildings, he never went inside because the buildings seemed too good for him.  He did not want the same thing for his son.
6. The Sound of Music / West Side Story  (1965 and 1961).  What do these musicals about singing in the Alps during WWII and dancing in the mean streets of 1950s New York,  have to do with Indiana?  The answer is Winchester native (also my birthplace) and legendary filmmaker Robert Wise, who produced and directed both.  For his efforts, Hoosier Wise earned the Academy Awards for Best Picutre and Best Director in both years.  In 1998, Wise was awarded the American Film Institute's Lifetime Achievement Award. 
7. OUT OF AFRICA (1985) This magnificent romantic epic stars Robert Redford and Meryl Streep as star-crossed lovers on the plains of East Africa in the years surrounding WWI.  So what's the Indiana connection?  The movie won Best Picture and Best Director Academy awards for producer/director Sydney Pollack -- a who was born and raised in Lafayette.  Pollack has directed some of Hollywood's most acclaimed movies (The Way We Were, Three Days of the Condor, Tootsie, The Firm), and has occasionally starred in supporting roles in front of the camera (Woody Allen's Husbands and Wives, and Stanley Kubrick's Eyes Wide Shut)