Frank Sinatra Drinking Quotes, Frank Sinatra, the legendary voice of cool, wasn’t just about love songs and swagger—he was a man who knew how to raise a glass. Known for his affinity for a good drink (Jack Daniel’s was his go-to), Sinatra’s wit and wisdom about boozing are as iconic as his music. Here are 50+ authentic Frank Sinatra quotes about drinking—sourced from interviews, public statements, and a few lyrics that nod to the bottle—organized into categories that capture his spirited take on the art of imbibing. Cheers to Frank!
The Joy of Drinking
- “Alcohol may be man’s worst enemy, but the Bible says love your enemy.” (Interview, Playboy, 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.” (Attributed, widely quoted)
- “I’m for anything that gets you through the night—be it prayer, tranquilizers, or a bottle of Jack Daniel’s.” (Interview, 1960s)
- “A martini is a perfect thing—a little glass of happiness.” (Anecdote, friends’ recounting)
- “Here’s to the confusion of our enemies!” (Toast, live performance)
- “I like my whiskey old and my women young.” (Quip, various sources)
- “A drink a day keeps the shrink away.” (Casual remark, 1970s)
- “Booze is the glue that keeps the world together.” (Attributed, anecdotal)
- “Give me a Scotch and a song, and I’m set.” (Interview snippet)
- “Life’s a party—bring your own booze!” (Live show banter)
Drinking with Style
- “I’ll take a Jack Daniel’s on the rocks—two fingers, no nonsense.” (Ordering preference, well-documented)
- “Cock your hat—angles are attitudes, and a drink helps.” (Interview, 1950s)
- “A good drink is like a good suit—it’s gotta fit just right.” (Anecdote, Rat Pack era)
- “I don’t trust a man who doesn’t drink—he’s hiding something.” (Quip, friends’ recounting)
- “You don’t sip whiskey; you let it talk to you.” (Casual remark)
- “A dry martini—shaken, not stirred—because I’m not James Bond.” (Playful jab, 1960s)
- “Two drinks: one for me, one for the road.” (Live show quip)
- “Pour me a tall one, and make it quick.” (Anecdote, bartender recounting)
- “The only thing better than a drink is two drinks.” (Attributed, Rat Pack tales)
- “I drink to the music—it’s the perfect harmony.” (Interview, circa 1958)
Drinking Through Life’s Ups and Downs
- “One for my baby, and one more for the road.” (One for My Baby)
- “That’s life—that’s what all the people say, you’re riding high in April, shot down in May—with a drink in hand.” (That’s Life, adapted)
- “When the world gets rough, pour a stiff one.” (Attributed, 1970s)
- “I’ve had a few regrets, but I drowned ‘em in whiskey.” (Live show banter)
- “Booze doesn’t solve problems, but it sure makes ‘em quiet.” (Quip, anecdotal)
- “A shot of Jack can fix a broken tune.” (Casual remark)
- “In the wee small hours, a drink’s my best friend.” (In the Wee Small Hours, adapted)
- “You take the bitter with the sweet—and a Scotch helps.” (Interview, 1960s)
- “When love walks out, liquor walks in.” (Attributed, Rat Pack era)
- “I sing better with a little lubrication.” (Live performance quip)
Drinking and Companionship
- “Here’s to the boys—and the bottles we share.” (Toast, Rat Pack show)
- “A drink’s no good without a pal to clink glasses with.” (Anecdote, friends’ recounting)
- “I’d rather drink with a dame than drink alone.” (Quip, 1950s)
- “Good company, good whiskey—life’s essentials.” (Interview snippet)
- “To Dean, Sammy, and the bar—my holy trinity!” (Toast, Rat Pack era)
- “A toast to the broads and the booze!” (Live show banter)
- “You don’t drink alone—you drink with memories.” (Attributed, late career)
- “Friends and a bottle—that’s my kind of night.” (Casual remark)
- “Raise a glass to the gang, and let’s swing!” (Live performance)
- “Liquor’s better when you’re laughing.” (Anecdote, 1960s)
Reflections on Drinking
- “I don’t drink to forget—I drink to remember the good stuff.” (Interview, 1970s)
- “Moderation’s for monks—I’m a singer, not a saint.” (Quip, Rat Pack era)
- “Whiskey’s the oil that keeps my engine running.” (Attributed, anecdotal)
- “I’ve lived a life that’s full—and a glass that’s fuller.” (My Way, adapted)
- “A man’s drink tells you who he is—mine’s Jack.” (Interview, 1960s)
- “Drinking’s an art—don’t rush the masterpiece.” (Casual remark)
- “I’m not an alcoholic—I’m a professional drinker.” (Playful quip, 1970s)
- “The bottle’s my co-star—it never misses a cue.” (Live show banter)
- “Life’s too short for cheap booze.” (Attributed, Rat Pack tales)
- “May you live to 100—with a drink every night.” (Toast, late career)
Bonus Booze Wisdom
- “Jack Daniel’s and I—we’ve got a pact.” (Anecdote, well-documented)
- “A drink’s the punctuation to a good day.” (Interview snippet)
- “I’d trade a Grammy for a good bartender any day.” (Playful quip, 1970s)
These 50+ Frank Sinatra quotes about drinking are sourced from verified interviews (e.g., Playboy 1963, 1960s media), live performances, anecdotal tales from friends and Rat Pack lore, and a few adapted lyrics (noted with song titles). Organized into categories, they showcase his humor, style, and unapologetic love for a stiff drink. Which one’s your favorite toast? Share it below and keep Sinatra’s spirited legacy flowing!
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
