- Oakie fought with cameramen for years about screen makeup -- he never wore any and refused to wear makeup under any circumstances.
- Working as a Wall Street clerk, he narrowly escaped death in 1920 after the Treasury Building was bombed by terrorists.
- His first job was as a telephone clerk for a brokerage firm. The clerks let off steam by pelting each other with cream filled pies. Someone recognised his comic potential and asked him to appear in an annual show of the Cardiac Society for Wall Street executives. The director of the show, May Leslie, eventually persuaded Oakie to quit his job and become an actor. He was first on stage proper, in the chorus of George M. Cohan's 'Little Nellie Kelly' in 1922. He then formed a popular vaudeville double act with Lulu McConnell. From there on,the rest is history.
- Oakie did not enjoy working with Spencer Tracy in Looking for Trouble (1934) because Tracy had the habit of mumbling his lines for a natural effect. Oakie had too hard a time reading his lips in their shared scenes. They never worked together again.
- Dubbed "The World's Oldest Freshman" because he was rather long in the tooth (30 something) for the collegiates he was asked to play, including roles in College Humor (1933), College Rhythm (1934), and Collegiate (1935). In the movie Rise and Shine (1941), the 38-year-old was asked to play an 18-year-old senior.
- When a shocked Jack told Chaplin that maybe he should find an Italian actor to play "Il Duce" in The Great Dictator (1940), Chaplin supposedly told him, "What's funny about an Italian playing Mussolini?" Chaplin, in a Hitler parody, and Oakie were both nominated for acting Oscars.
- On October 19, 1959, was a pallbearer at Errol Flynn's funeral along with Raoul Walsh, Mickey Rooney, 'Guinn "Big Boy' Williams', Mike Romanoff and Otto Reichow at the Church of the Recessional at Forest Lawn, Glendale, CA.
- Refused to appear on talk shows because they only paid scale.
- Worked at Paramount, 1928-36; RKO 1936-38; 20th Century Fox, 1940-43; and Universal 1944-45. At the peak of his popularity, in the 1940's, he earned up to $7,500 a week.
- His stage name was taken from his mother's maiden name, Evelyn Oakie.
- In 1981, the Academy of Motion Picture Arts and Sciences established the Jack Oakie Lecture on Comedy in Film, as an annual event.
- He and his wife Victoria spent their entire marriage living on a 10-acre estate in the San Fernando Valley near Los Angeles.
- Jack's widow, Victoria Horne wrote a book called When the Line Is Straight: Jack Oakie's Comedy and Motion Pictures in 1997.
- Divorced from actress Venita Varden in 1945, she was among the many who perished in a June 17, 1948 plane crash on the Aristes mountain near Wilburton, Pennsylvania, that killed 43 passengers in all. Also included were night club owner Earl Carroll, famous for his Vanities Showgirls, and his leading lady, showgirl Beryl Wallace.
- His boisterous "Benzino Napaloni" in Charlie Chaplin's satire The Great Dictator (1940) is based on Italy's Benito Mussolini.
- It's been often stated that Jack and Charles Chaplin never spoke after filming The Great Dictator (1940) because Chaplin was upset that Oakie stole the picture away from him, receiving an Oscar nomination.
- Jack is mentioned in the Coen Brothers film Barton Fink (1991), which is set in Hollywood during the 1940s.
- A small display celebrating the comedy and fame of Jack is at the Motion Picture & Television Country House and Hospital in Woodland Hills, California. There is also a plaque in the ground in front of the home where he was born in Sedalia, Missouri.
- For many years, he lived on a ranch in the San Fernando Valley with his wife, the actress Victoria Horne.
- Once teamed with fellow vaudevillian Richard 'Skeets' Gallagher in the hopes of being another Stan Laurel and Oliver Hardy, but it didn't pan out. They did perform in six films together.
- He died only 29 days after his The Great Dictator (1940) co-star and director Charles Chaplin.
- Son of actress Evelyn Oakie.
- During the shoot of the film Navy Blues (1941), he presented Ann Sheridan with a washtub filled with flowers. Ann once played a bit part as a laundress in one of Oakie's early vehicles.
- Jack Oakie's star on the Hollywood Walk of Fame is at 6752 Hollywood Boulevard, and his hand and footprints can be found at Grauman's Chinese Theater in Hollywood.
- Interred at Forest Lawn, Glendale, CA., in the Whispering Pines section at the top of the hill.
- His mother worked as a teacher in New York at the time Oakie studied business at De La Salle School.
- Stepson-in-law of Cleo Ridgely.
- Stepbrother-in-law of June Harris and James Horne Jr..
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