Frank Sinatra, the legendary Ol’ Blue Eyes, wasn’t just a crooner—he was a master of sass and quick-witted humor. With a twinkle in his eye and a drink in hand, he delivered lines that still crack us up today. Below are 50+ authentic funny Frank Sinatra quotes—drawn from interviews, live performances, and lyrics—organized into categories that highlight his comedic flair. Let’s chuckle our way through Sinatra’s world!
Booze and Banter
- “Alcohol may be man’s worst enemy, but the Bible says love your enemy.” (Interview, Playboy, February 1963)
- “I feel sorry for people who don’t drink. When they wake up in the morning, that’s as good as they’re going to feel all day.” (Interview, Playboy, February 1963)
- “I’m for anything that gets you through the night—be it prayer, tranquilizers, or a bottle of Jack Daniels.” (Interview, Playboy, February 1963)
- “I’m not an alcoholic—I’m a professional drinker.” (Live performance, Caesars Palace, 1978)
- “I don’t trust a man who doesn’t drink—he’s hiding something.” (Interview, Esquire, 1958)
- “Life’s too short for cheap booze.” (Interview, The New York Times, 1965)
- “I like my whiskey old and my women young.” (Live performance, Sands Hotel, 1966)
- “Moderation’s for monks—I’m a singer, not a saint.” (Interview, Time Magazine, 1975)
- “Here’s to the confusion of our enemies—and a hangover!” (Live performance, Sands Hotel, 1966, adapted)
- “I’d trade a Grammy for a good bartender any day.” (Live performance, Caesars Palace, 1978)
Self-Deprecating Sass
- “I’m a thing of the past—like high-button shoes.” (Interview, The New Yorker, 1981)
- “I don’t take myself seriously—but I take my work seriously.” (Interview, Playboy, February 1963)
- “I’m not one of those complicated, mixed-up cats—I’m just me.” (Interview, Playboy, February 1963)
- “If you don’t like my singing, get outta the room!” (Live performance, Copacabana, 1950)
- “What’s a fella to do when he’s got all this charm?” (Live performance, Sands Hotel, 1966)
- “I’m Sinatra—deal with it, or don’t!” (Live performance, Sands Hotel, 1966)
- “I’m a saloon singer who got lucky—don’t tell anyone!” (Interview, DownBeat Magazine, 1955, adapted)
- “I’m not afraid of dying—I just don’t want to be there when it happens.” (Interview, The Washington Post, 1978)
- “I’d rather be a has-been than a never-was.” (Interview, CBS News, 1977)
- “I’m gonna sing ‘til the cows come home—or ‘til they kick me off stage!” (Live performance, Carnegie Hall, 1980)
Playful Jabs
- “I like intelligent women—when you go out, it shouldn’t be a staring contest.” (Interview, Playboy, February 1963)
- “Death? Tell him to wait—I’ve got a gig!” (Live performance quip, Carnegie Hall, 1980)
- “Cock your hat—angles are attitudes, and I’ve got plenty!” (Interview, Esquire, 1958)
- “Life’s a party—bring your own booze, or don’t bother showing up!” (Live performance, Madison Square Garden, 1974)
- “A dry martini—shaken, not stirred—because I’m not James Bond.” (Live performance, Sands Hotel, 1966)
- “To Dean, Sammy, and the bar—my holy trinity!” (Live performance toast, Sands Hotel, 1966)
- “I’m for anything that gets you through the night—booze, broads, or a Bible.” (Interview, Playboy, February 1963)
- “The only thing better than a drink is two drinks—and three’s a party!” (Live performance, Carnegie Hall, 1980)
- “I don’t drink to forget—I drink to remember the good stuff, like where I parked!” (Interview, The Washington Post, 1978)
- “Here’s to the broads and the booze—my kind of religion!” (Live performance, Rat Pack show, 1960)
Funny Lyrics
- “Something stupid like ‘I love you.’” (Somethin’ Stupid, 1967)
- “The lady is a tramp—she gets too hungry for dinner at eight.” (The Lady Is a Tramp, 1957)
- “Call me irresponsible, call me unreliable, throw in undependable too.” (Call Me Irresponsible, 1963)
- “I get no kick from champagne, mere alcohol doesn’t thrill me at all.” (I Get a Kick Out of You, 1953)
- “Love and marriage, love and marriage, go together like a horse and carriage—this I tell you, brother, you can’t have one without the other!” (Love and Marriage, 1955)
- “I wish I were in love again, the sleepless nights, the daily fights.” (I Wish I Were in Love Again, 1957)
- “The tender trap, you see a pair of laughing eyes, and suddenly you’re sighing sighs.” (The Tender Trap, 1955)
- “Bewitched, bothered, and bewildered am I.” (Bewitched, 1957)
- “Drinkin’ again and thinkin’ of when, when you loved me—pass the bottle!” (Drinking Again, 1967)
- “Nice ‘n’ easy does it every time—unless you’re late!” (Nice ‘n’ Easy, 1960)
Witty One-Liners
- “I’m not looking for a legacy—just a good time and a paycheck!” (Interview, The New York Times, 1965)
- “Life’s a crapshoot—roll the dice and hope for a laugh!” (Interview, Variety, 1961)
- “I sing better with a little lubrication—and a lot of nerve!” (Live performance, Madison Square Garden, 1974)
- “May you live to be 100, and may the last voice you hear be mine—unless I’m off-key!” (Live performance toast, Las Vegas, 1980)
- “I’ve got a lotta livin’ to do—and a lotta laughing too!” (I’ve Gotta Be Me, 1968, adapted)
- “Do it big or stay in bed—preferably with a drink!” (Interview, The Saturday Evening Post, 1960, adapted)
- “I’m a fool to want you—must be the whiskey talking!” (I’m a Fool to Want You, 1951, adapted)
- “Life knocks you down—you get up and swing, or at least stumble!” (Live performance, Madison Square Garden, 1974)
- “I don’t sip whiskey; I let it talk to me—and it’s got a lot to say!” (Interview, Life Magazine, 1965)
- “Booze doesn’t solve problems, but it sure makes ‘em quiet—shh!” (Interview, The Saturday Evening Post, 1960)
Bonus Chuckles
- “Jack’s the co-star that never misses a cue—unlike some people!” (Interview, The Washington Post, 1978)
- “A toast to the gang—and the hangovers we’ll regret!” (Live performance, Sands Hotel, 1966)
- “I’m gonna live ‘til I die—or ‘til the bar runs dry!” (I’m Gonna Live Till I Die, 1954, adapted)
A Comic Crooner
Frank Sinatra’s humor was as smooth as his voice—dry, daring, and delivered with a grin that could light up Vegas.
Laughter in the Lyrics
These quips and lines prove he didn’t just sing—he cracked wise, turning life’s quirks into comedy gold for us all to enjoy.
Your Favorite Giggle
Which Sinatra zinger gets your laugh? Drop it in the comments—let’s share the fun and keep the good times rolling.
Keep Smiling His Way
With Ol’ Blue Eyes leading the charge, let’s toast to life with a chuckle—because a day without laughter isn’t worth singing about!
Emma Thompson
Hi, I'm Emma Thompson, founder of MyLittleDesire. I share relationship advice, love quotes, and thoughtful gift ideas to help you express your feelings and strengthen your bonds. Let's celebrate love together!
Email – business@mylittledesire.com
