- Barry Levinson has referenced Sinatra in a couple of his movies:
- In Diner, early on, Eddie is often asking his friends whom they prefer as musicians, Sinatra or Johnny Mathis.note
- In Good Morning, Vietnam, when Lt. Hauk is telling the radio staff what kind of music he deems acceptable to play at the station, he includes, "Certain ballads by Mr. Frank Sinatra."
- In Liberty Heights, Ben is obsessed with Sinatra, to the point he refuses to leave the car until the song Sinatra is singing that's on the radio finishes playing; as he tells the disbelieving driver (the father of the girl Ben has a crush on), "You don't walk out on Frank, sir. It would be too disrespectful."
- Who Framed Roger Rabbit: During his fight with Judge Doom at the Acme warehouse, Eddie Valiant picks up an ACME Singing Sword, but it turns out to be a toon caricature of Frank Sinatra singing "Witchcraft".
- In Call Me Bwana, Matt tells the angry Ekele tribesmen that John F. Kennedy sent him. When they don't care, he lists various other Kennedies, then Frank Sinatra.
- In Zebrahead (1992), Zack's dad recommends Frank Sinatra as music for a romantic seduction.
- In The Idolmaker, Vinny lists Frank Sinatra as the kind of dark-haired Teen Idol there's demand for.
- Ocean's Thirteen (the second sequel to a Rat Pack movie, no less), both Reuben and Willy Bank belong to a group of old school Vegas moneymen who have shaken Sinatra's hand.
- In the Carl Hiaasen novel Native Tongue, Jim Tile expresses impatience with "white people's music", and says the only non-black artist he likes is Sinatra.
- Early from Navigating Early listens to Frank Sinatra on Wednesdays.
- The Boy Who Drew Monsters: When Miss Tiramaku goes to talk to Jack Peter, Tim, who disapproves of her, puts on a Frank Sinatra record so he and Holly can have a private conversation about her.
- In Bewilderment, Robin sings "High Hopes," which his mother used to sing when he was an infant.
- In Apollo Autism, Max and Jane listen to "Fly Me to the Moon" while they mourn the news of the Apollo 1 fire.
- In The Love Boat episode "Sounds of Silence," an aging shock rocker tells his manager, "I'm a singer!" His manager replies, "Sinatra is a singer. Lou Rawls is a singer. You are an attraction."
Music
- Bon Jovi's "It's My Life" has the line "My heart is like an open highway\Like Frankie said, I did it my way"
- David Bowie's "Life on Mars?" was written as a riff on "My Way", playing off of the fact that Sinatra's folks preferred it over Bowie's "Even a Fool Learns to Love", both English versions of Claude François' "Comme d'Habitude".
- Looney Tunes: Frankie was a common target for the Warner Bros. animators during his early career in the 1940s, with most of the jokes focusing on his gaunt physique (with implications of him being sickly thrown in for good measure) and the frenzied reactions of his young female audience.
- In "Swooner Crooner", he is caricatured as a rooster so thin he disappears behind the microphone stand. His crooning distracts Porky's chickens from laying eggs; ironically, when he's competing with a rooster version of Bing Crosby, his singing causes them to lay eggs by the hundreds.
- Sinatra appears as a rooster again in "Curtain Razor", alongside Bing Crosby as a parrot and Al Jolson as a duck, auditioning for talent agent Porky Pig.
- In "Book Revue", Sinatra appears in the cover of Voice in the Wilderness, being pushed on a wheelchair by a hospital orderly. His rendition of "It Had to Be You" made all the women in the bookstore swoon, including the Big Bad Wolf, who faints right into a copy of Dante's Inferno.
- "Catch as Cats Can" features a canary version of Sinatra, who eats vitamins instead of bird seed. A parrot Bing Crosby, annoyed by his singing, convinces a cat (an early version of Sylvester) to eat the Sinatra canary because he's full of vitamins.
- "Quentin Quail" is about a quail trying to catch a worm for his daughter. When he finally gives it to her, she rejects it because it looks like Frankie Sinatra and can't bear eating him.
- In the Bugs Bunny cartoon "The Unruly Hare", Bugs hears Elmer's singing and snarks "That sounds like Frankie Sinatra, or an unreasonable facsimile."
- On "Long-Haired Hare", one of the tricks Bugs plays on pompous opera singer Giovanni Jones is to dress as a teenage girl wanting his autograph (with a dynamite stick for a pen), saying that "Frankie and Perry (Como) just aren't in it; you're my swooner dreamboat!"
- In "Slick Hare", Sinatra is struggling to sip a drink from a straw, eventually getting sucked into the straw itself.
- Tex Avery MGM Cartoons: "Little 'Tinker" has a skunk dress as Sinatra to get girls. As he sings "All or Nothing At All", a crowd of bunnies gathers around him and react not unlike Wolfie towards Red in "Red Hot Riding Hood". Gags include the skunk disappearing behind his microphone, slipping through a knothole, being outweighed by a feather, being connected to plasma, in an iron lung and getting measured by an undertaker.
- The Ren & Stimpy Show: In "Ol' Blue Nose", Stimpy gets hit in the nose and suddenly starts singing like Sinatra, becoming a big hit.
- The Walter Lantz cartoon "The Pied Piper of Basin Streetnote " is a Setting Update version of The Pied Piper of Hamelin, with the Piper as a swing trombonist. When he's stiffed by the mayor, he transforms into "Hank Swoonatra" and leads away the children — specifically the teenage girls — to a riverboat swing cruise.
