"If you hear Bing Crosby trying to swing, it doesn't work. He swings like a rusty gate"
About this Quote
The intent is performative authority. Stallone isn’t arguing; he’s auditioning his ear. By naming Crosby - a near-sacred American icon - he signals that no legacy is too big to be dragged into the garage and tested for squeaks. That irreverence is the point: it positions Stallone as the guy who values feel over prestige, groove over pedigree. There’s also a subtext about authenticity that’s deeply showbiz. Swing, in this framing, isn’t something you can simply “try” on like a jacket. You either have the rhythmic ease or you don’t, and “trying” becomes the tell that you’re faking it.
Contextually, it’s a late-20th-century generational flex: a newer entertainment class side-eyeing the old network-era gentility. Crosby represents polished, controlled charm; Stallone champions a rougher standard where technique without looseness reads as mechanical. The insult is funny because it’s vivid, but it also maps a whole cultural argument about who gets to sound “natural” on a mic.
Quote Details
| Topic | Witty One-Liners |
|---|---|
| Source | Help us find the source |
| Cite |
Citation Formats
APA Style (7th ed.)
Stallone, Frank. (2026, January 16). If you hear Bing Crosby trying to swing, it doesn't work. He swings like a rusty gate. FixQuotes. https://fixquotes.com/quotes/if-you-hear-bing-crosby-trying-to-swing-it-doesnt-121789/
Chicago Style
Stallone, Frank. "If you hear Bing Crosby trying to swing, it doesn't work. He swings like a rusty gate." FixQuotes. January 16, 2026. https://fixquotes.com/quotes/if-you-hear-bing-crosby-trying-to-swing-it-doesnt-121789/.
MLA Style (9th ed.)
"If you hear Bing Crosby trying to swing, it doesn't work. He swings like a rusty gate." FixQuotes, 16 Jan. 2026, https://fixquotes.com/quotes/if-you-hear-bing-crosby-trying-to-swing-it-doesnt-121789/. Accessed 6 Feb. 2026.


