Elvira Plunkett (Page), beauty queen and the pride of Gopher City, Kansas, wins a contest and goes off to Hollywood to become an actress. With her is her overbearing stage mom (Trixie Friganza) and her bumbling friend and manager, Elmer J. Butts (Keaton). On the train to Hollywood, they meet a Hollywood movie star, Larry Mitchell (Montgomery) who is enchanted with the lovely Elvira. This is greatly upsetting to Elmer, who loves Elvira, although she doesn't know it.
Elvira actually isn't all that interested in being a movie actress, but Larry gets her into MGM. More surprisingly, he eventually gets Elmer a movie contract, despite Elmer horribly botching his lines in his first screen test. Eventualy, Elmer becomes a movie star of his own—but will he win Elvira's hand?
Free and Easy was Keaton's talking film debut. It actually did well at the box office, even though MGM had little idea of how to translate Keaton's talent to talking pictures. However, in hindsight it's seen as the beginning of Keaton's disastrous career slide that saw him eventually fired from MGM in 1933, with his starring film career over for good.
There was a Spanish-language remake, Estrellados, that was shot immediately after this one, as was common practice for a little while in the early talkie days. Keaton learned his part phonetically.
- As Himself: Fred Niblo, a real MGM director, has a supporting part as Fred Niblo, an MGM director who is driven to distraction by Elmer's bumbling incompetence as a performer.
- Bad "Bad Acting": Keaton, as Elmer, being hopelessly incompetent as a dramatic actor. Eventually he gets hired as a comedy star.
- Bedlah Babe: Elmer's film seems to have some vaguely Arab setting, so Mimi, the girl he's paired up with, is dressed this way.
- The Cameo: Several MGM stars and directors make cameos—Jackie Coogan, William Haines, Cecil B. DeMille, Dorothy Sebastian, Karl Dane, and Lionel Barrymore. Part of the Harsher in Hindsight nature of this film is how many careers went south right after this movie. William Haines, who was gay, was soon canned by MGM after he refused to marry The Beard; he spent the rest of his life as an interior decorator. Karl Dane was fired by MGM not long after this due to his thick Danish accent; he was unemployed and completely broke by the time he killed himself in 1934.
- Cannot Spit It Out: Elmer never can bring himself to say that he loves Elvira, despite having multiple chances to do so. This eventually ends with him losing her.
- Did Not Get the Girl: Elmer, as Elvira accepts Larry's proposal. This is a first in the Buster Keaton filmography, as he always got the girl in his silent days, even if he didn't seem particularly interested in the girl.
- The Ditz: Elmer is a bumbling dimwit, ruining multiple film shoots, unable to understand instructions to recite a single line of dialogue. One of the reasons this film is unpopular among latter-day Keaton fans is his dumb character here contrasting poorly with the can-do problem solvers of his silent film days.
- Downer Ending: Elmer doesn't get the girl, and is left Alone in a Crowd on the film set.
- Embarrassing Last Name: Elmer Butts.
- Grievous Bottley Harm: Ma Plunkett crashes a vase over Larry's head after being brought to Larry's attempted seduction of Elvira.
- Have a Gay Old Time: "I suppose you make violent love to every girl you meet."
- Just Friends: Elmer and Elvira, much to his displeasure.
- Ladykiller in Love: Larry. After his attempt at sex with Elvira goes awry, he's embarrassed, and he pursues her more sincerely.
- Love Interest: Anita Page has little to do in this movie as Elvira has hardly any detail to her character other than being the attractive Love Interest for both Larry and Elmer. She doesn't even get to do any performing, as her experience on the MGM set amounts to watching Larry and Elmer performing.
- Love Triangle: Elmer and Larry, rivals for Elvira.
- Oblivious to Love: Elvira never does catch on that Elmer is in love with her.
- One Dialogue, Two Conversations: After getting hired as a comedy star, Elmer tries to confess his feelings to Elvira. But since he Cannot Spit It Out he resorts to awkward circumlocutions—"What would you say if a certain movie star proposed to you?"—and Elvira thinks that Elmer is being The Matchmaker on Larry's behalf.
- Plunger Detonator: In use on Karl Dane and Dorothy Sebastian's film set; Elmer puts his foot on it and blows up the charge, ruining the shot.
- Remake Cameo: Page and Montgomery have cameos as themselves in Estrellados.
- Repeat After Me: A long sequence between Elmer and Fred Niblo, in which Niblo's instructions—"Listen, say it after me, The queen has swooned"—result in this trope.
- Stage Mom: Domineering Ma Plunkett, determined to make her daughter a movie star when Elvira isn't that interested.
- Title Drop: "Free and Easy" is a musical number Elmer performs in towards the end.