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Advice Songs from the 1890s to the 1950s: Life Lessons, Warnings, Wisdom, and Old-Fashioned Common Sense

Advice songs have been part of popular music for generations. Long before advice columns, podcasts, social media threads, and “let me tell you what you should do” relatives, singers were already giving listeners warnings, comfort, encouragement, romantic guidance, moral lessons, and the occasional nudge toward better judgment.

Some advice songs are gentle. Some are funny. Some are bossy. Some are heartbreaking. Some offer wisdom learned the hard way. Others sound like someone’s grandmother, preacher, drinking buddy, dance partner, or regretful ex decided to make a record. That is a pretty strong committee.

This list focuses on advice songs from the 1890s through the 1950s, with a few early-1960s edge records where the old-fashioned advice-song spirit still fits. The songs include pop standards, country warnings, blues lessons, jazz wisdom, Broadway numbers, folk reflections, novelty songs, and classic oldies about choices, consequences, love, patience, work, luck, and learning when to listen.

As Doris Day sang in Que Sera, Sera (Whatever Will Be, Will Be), “what will be, will be.” Of course, people have been ignoring good advice since long before the phonograph, so the songs below had plenty to work with.

Best Advice Songs from the 1890s to the 1950s

These are the strongest starting points for an old-fashioned advice songs playlist. They are memorable, culturally useful, easy to understand, or built around advice that still makes sense today.

  1. Que Sera, Sera (Whatever Will Be, Will Be) – Doris Day
  2. It’s All in the Game – Tommy Edwards
  3. Don’t Take Your Guns to Town – Johnny Cash
  4. Sixteen Tons – Tennessee Ernie Ford
  5. High Hopes – Frank Sinatra
  6. Keep On the Sunny Side – The Carter Family
  7. Count Your Blessings (Instead of Sheep) – Bing Crosby / Rosemary Clooney
  8. It Don’t Mean a Thing (If It Ain’t Got That Swing) – Duke Ellington
  9. Pack Up Your Troubles in Your Old Kit-Bag (and Smile, Smile, Smile) – Knickerbocker Quartet
  10. Enjoy Yourself (It’s Later Than You Think) – Guy Lombardo / Doris Day

Advice Songs by Style

Life Advice, Wisdom, and Acceptance Songs

Some advice songs tell listeners to accept uncertainty, keep perspective, count blessings, smile through trouble, or avoid making every problem heavier than it already is. That advice may sound simple, but simple advice is often the first thing people ignore.

  • Que Sera, Sera (Whatever Will Be, Will Be) – Doris Day
  • It’s All in the Game – Tommy Edwards
  • High Hopes – Frank Sinatra
  • Count Your Blessings (Instead of Sheep) – Bing Crosby / Rosemary Clooney
  • Keep On the Sunny Side – The Carter Family
  • When You’re Smiling – Louis Armstrong / Seger Ellis
  • Smile and the World Smiles with You – Lewis James & The Peerless Quartet
  • Little Things Mean a Lot – Kitty Kallen
  • It’s the Little Things That Count – Bunny Berigan
  • Faith Can Move Mountains – Nat King Cole
  • Easy Come, Easy Go – Eddy Duchin
  • Life Begins When You’re in Love – Isham Jones

Romantic Advice and Relationship Warnings

Love songs often come with advice, even when the advice is messy. These songs warn about heartbreak, patience, jealousy, forgiveness, commitment, regret, and the classic problem of telling someone what to do while also being completely lovestruck.

  • Who’s Sorry Now? – Connie Francis
  • Too Young – Nat King Cole
  • Wear My Ring Around Your Neck – Elvis Presley
  • Save the Last Dance for Me – The Drifters
  • Put Your Head on My Shoulder – Paul Anka
  • It’s Not for Me to Say – Johnny Mathis
  • Chances Are – Johnny Mathis
  • A Lover’s Question – Clyde McPhatter
  • You Always Hurt the One You Love – The Mills Brothers
  • Let’s Call the Whole Thing Off – Fred Astaire
  • Don’t Sit Under the Apple Tree (With Anyone Else but Me) – The Andrews Sisters / Glenn Miller
  • If We Can’t Be the Same Old Sweethearts, We’ll Just Be the Same Old Friends – Irving Kaufman

Warnings, Regret, and Consequences

Some advice songs are warnings from people who have already learned the lesson. That makes them useful, dramatic, and occasionally too late. The best warning songs do not just say “don’t do that.” They show what happens after someone does it anyway.

  • Don’t Take Your Guns to Town – Johnny Cash
  • Sixteen Tons – Tennessee Ernie Ford
  • Get a Job – The Silhouettes
  • Smoke! Smoke! Smoke! (That Cigarette) – Tex Williams
  • Cigarettes, Whiskey, and Wild, Wild Women – Red Ingle
  • Alcoholic Blues – Billy Murray
  • Regretful Blues – Nora Bayes
  • I’m Wasting My Tears on You – Tex Ritter
  • Blame It on My Youth – Jan Garber
  • A Good Man Is Hard to Find – Marion Harris
  • Fools Rush In (Where Angels Fear to Tread) – Glenn Miller
  • Time Waits for No One – Helen Forrest

Work, Money, Luck, and Getting By

Advice songs often deal with practical life: work, debt, money, luck, ambition, and trying to keep going when the world has other plans. These songs may sound old, but the advice still shows up every Monday morning.

  • Sixteen Tons – Tennessee Ernie Ford
  • Get a Job – The Silhouettes
  • Nice Work If You Can Get It – Fred Astaire
  • The Best Things in Life Are Free – George Olsen
  • Ev’ry Little Bit Helps – Len Spencer & Ada Jones
  • Feather Your Nest – Henry Burr & Albert Campbell
  • Dreams Are a Dime a Dozen – Vaughn Monroe
  • Fancy You Fancying Me – Lewis James
  • Easy Come, Easy Go – Eddy Duchin
  • I Don’t Know Where I’m Going, but I’m on My Way – Peerless Quartet

Jazz, Swing, and Standards with Advice Built In

Jazz and swing standards often delivered advice with style. The message might be about rhythm, romance, confidence, or not taking life too stiffly. In these songs, good judgment arrives with a horn section, which honestly improves most advice.

  • It Don’t Mean a Thing (If It Ain’t Got That Swing) – Duke Ellington
  • Take the “A” Train – Duke Ellington
  • Undecided – Ella Fitzgerald with Chick Webb
  • Fools Rush In (Where Angels Fear to Tread) – Glenn Miller
  • When You’re Smiling – Louis Armstrong / Seger Ellis
  • Learnin’ the Blues – Frank Sinatra
  • Laughing on the Outside (Crying on the Inside) – Dinah Shore / Sammy Kaye
  • I’m Putting All My Eggs in One Basket – Fred Astaire
  • They Can’t Take That Away from Me – Fred Astaire / Ozzie Nelson
  • It Ain’t Necessarily So – Bing Crosby / Leo Reisman

Broadway, Movies, and Character Advice Songs

Stage and movie songs are full of advice because characters often sing when they cannot quite solve their own problems. Sometimes the advice is wise. Sometimes it is comic. Sometimes it is exactly what the character should have listened to earlier.

  • Que Sera, Sera (Whatever Will Be, Will Be) – Doris Day, from The Man Who Knew Too Much
  • Whistle While You Work – The Seven Dwarfs, from Snow White and the Seven Dwarfs
  • If I Only Had a Brain – The Scarecrow, from The Wizard of Oz
  • Soliloquy – Billy Bigelow, from Carousel
  • Sit Down, You’re Rockin’ the Boat – from Guys and Dolls
  • How Could You Believe Me When I Said I Loved You When You Know I’ve Been a Liar All My Life? – Fred Astaire & Jane Powell
  • Don’t Fence Me In – Cole Porter
  • Let’s Misbehave – Ben Bernie
  • Come On-a My House – Rosemary Clooney

Blues, Country, Folk, and Plainspoken Advice

Blues, country, and folk songs often give advice the hard way: through regret, survival, work, heartbreak, bad choices, and the kind of wisdom nobody learns from a pamphlet. These songs sound like experience with a melody attached.

  • Ramblin’ on My Mind – Robert Johnson
  • A Worried Man – The Kingston Trio
  • I Walk the Line – Johnny Cash
  • I’ll Forgive You, but I Can’t Forget – Roy Acuff
  • I Ain’t Gonna Play No Second Fiddle – Bessie Smith
  • ’Tain’t Nobody’s Business If I Do – Bessie Smith
  • Ain’t Nobody’s Business but My Own – Kay Starr
  • Back in the Saddle Again – Gene Autry
  • Pack Up Your Troubles in Your Old Kit-Bag (and Smile, Smile, Smile) – Knickerbocker Quartet

Overlap note: Advice songs often belong in more than one category. Sixteen Tons is a work song, a warning song, and a social-commentary record. Que Sera, Sera is a movie song, a life-advice song, and a parent-child song. Don’t Take Your Guns to Town is a country story song and one of the clearest warning songs in popular music.

1950s and Older Advice Songs Chart

  1. Que Sera, Sera (Whatever Will Be, Will Be) – Doris Day
  2. Who’s Sorry Now? – Connie Francis
  3. Too Young – Nat King Cole
  4. Wear My Ring Around Your Neck – Elvis Presley
  5. Whistle While You Work – The Seven Dwarfs
  6. Makin’ Whoopee! – Eddie Cantor
  7. Blues in the Night – Dinah Shore / Frank Sinatra
  8. Sixteen Tons – Tennessee Ernie Ford
  9. Ain’t That a Shame – Fats Domino
  10. Don’t Take Your Guns to Town – Johnny Cash
  11. Sit Down, You’re Rockin’ the Boat – from Guys and Dolls
  12. It’s Just a Matter of Time – Brook Benton
  13. Soliloquy – Billy Bigelow, from Carousel
  14. High Hopes – Frank Sinatra
  15. All I Have to Do Is Dream – The Everly Brothers
  16. It Don’t Mean a Thing (If It Ain’t Got That Swing) – Duke Ellington
  17. Save the Last Dance for Me – The Drifters
  18. Lady Sings the Blues – Billie Holiday
  19. Put Your Head on My Shoulder – Paul Anka
  20. It’s Not for Me to Say – Johnny Mathis
  21. Get a Job – The Silhouettes
  22. It’s All in the Game – Tommy Edwards
  23. I’ll Forgive You, but I Can’t Forget – Roy Acuff
  24. Don’t Fence Me In – Cole Porter
  25. Let’s Misbehave – Ben Bernie
  26. Chances Are – Johnny Mathis
  27. A Lover’s Question – Clyde McPhatter
  28. Eenie Meenie Miney Mo – Benny Goodman
  29. My Heart Is a Broken Book – Carl Dobkins Jr.
  30. Time Waits for No One – Helen Forrest
  31. If I Only Had a Brain – The Scarecrow, from The Wizard of Oz
  32. I Walk the Line – Johnny Cash
  33. Fools Rush In (Where Angels Fear to Tread) – Glenn Miller
  34. A Worried Man – The Kingston Trio
  35. Cigarettes, Whiskey, and Wild, Wild Women – Red Ingle
  36. Learnin’ the Blues – Frank Sinatra
  37. You Always Hurt the One You Love – The Mills Brothers
  38. It Ain’t Necessarily So – Bing Crosby / Leo Reisman
  39. When You’re Smiling – Louis Armstrong / Seger Ellis
  40. Little Things Mean a Lot – Kitty Kallen
  41. Ramblin’ on My Mind – Robert Johnson
  42. How Could You Believe Me When I Said I Loved You When You Know I’ve Been a Liar All My Life? – Fred Astaire & Jane Powell
  43. Show Me the Way to Go Home – Vincent Lopez
  44. If You Were in My Place (What Would You Do?) – Duke Ellington
  45. Undecided – Ella Fitzgerald with Chick Webb
  46. Wake the Town and Tell the People – Les Baxter
  47. Come On-a My House – Rosemary Clooney
  48. After You Get What You Want, You Don’t Want It – Van & Schenck
  49. I’m Wasting My Tears on You – Tex Ritter
  50. They Can’t Take That Away from Me – Fred Astaire / Ozzie Nelson
  51. Back in the Saddle Again – Gene Autry
  52. Absence Makes the Heart Grow Fonder – George J. Gaskin
  53. I Love My Wife, but Oh! You Kid – Arthur Collins / Bob Roberts / Edward M. Favor
  54. They’re Either Too Young or Too Old – Jimmy Dorsey
  55. Am I Blue? – Ethel Waters
  56. What Do I Have to Do (To Make You Love Me) – Vaughn Monroe
  57. Let’s Call the Whole Thing Off – Fred Astaire
  58. Don’t Sit Under the Apple Tree (With Anyone Else but Me) – Glenn Miller / The Andrews Sisters
  59. I Ain’t Gonna Play No Second Fiddle – Bessie Smith
  60. Take the “A” Train – Duke Ellington
  61. Don’t Telephone, Don’t Telegraph, Tell a Woman – Tex Williams
  62. The Best Things in Life Are Free – George Olsen
  63. Keep On the Sunny Side – The Carter Family
  64. ’Tain’t Nobody’s Business If I Do – Bessie Smith
  65. Alcoholic Blues – Billy Murray
  66. Faith Can Move Mountains – Nat King Cole
  67. Smile and the World Smiles with You – Lewis James & The Peerless Quartet
  68. It’s the Little Things That Count – Bunny Berigan
  69. Laughing on the Outside (Crying on the Inside) – Dinah Shore / Sammy Kaye
  70. Smoke! Smoke! Smoke! (That Cigarette) – Tex Williams
  71. I’m Putting All My Eggs in One Basket – Fred Astaire
  72. Easy Come, Easy Go – Eddy Duchin
  73. Tell Me Why – The Four Aces / Eddie Fisher
  74. It’s Easier Said Than Done – Guy Lombardo
  75. Just Another Day Wasted Away (Waiting for You) – Fred Waring’s Pennsylvanians
  76. For Every Boy Who’s Lonely, There’s a Lonely Girl – Lyric Quartet
  77. If You Knew Susie (Like I Know Susie) – Eddie Cantor / Cliff Edwards
  78. Can Anyone Explain? (No! No! No!) – The Ames Brothers
  79. Ain’t Nobody’s Business but My Own – Kay Starr
  80. Count Your Blessings (Instead of Sheep) – Bing Crosby / Rosemary Clooney
  81. You’re Driving Me Crazy – Guy Lombardo
  82. A Good Man Is Hard to Find – Marion Harris
  83. Dreams Are a Dime a Dozen – Vaughn Monroe
  84. Oh Dear! What Can the Matter Be? – Ella Logan
  85. Everything’s Been Done Before – Freddy Martin / Guy Lombardo
  86. Nice Work If You Can Get It – Fred Astaire
  87. If We Can’t Be the Same Old Sweethearts, We’ll Just Be the Same Old Friends – Irving Kaufman
  88. Forever Is a Long, Long Time – Charles Hart
  89. There’s a Lot of Things You Never Learn in School – Dan Quinn
  90. Life Begins When You’re in Love – Isham Jones
  91. Enjoy Yourself (It’s Later Than You Think) – Guy Lombardo / Doris Day
  92. I Don’t Know Where I’m Going, but I’m on My Way – Peerless Quartet
  93. Pack Up Your Troubles in Your Old Kit-Bag (and Smile, Smile, Smile) – Knickerbocker Quartet
  94. Blame It on My Youth – Jan Garber
  95. It’s Always June When You’re in Love – Reed Miller
  96. Regretful Blues – Nora Bayes
  97. Fancy You Fancying Me – Lewis James
  98. Ev’ry Little Bit Helps – Len Spencer & Ada Jones
  99. Feather Your Nest – Henry Burr & Albert Campbell
  100. Every Day’s a Holiday – Cab Calloway / Glenn Miller

Advice Songs Trivia

  • Que Sera, Sera (Whatever Will Be, Will Be) was introduced by Doris Day in Alfred Hitchcock’s The Man Who Knew Too Much and won the Academy Award for Best Original Song.
  • Sixteen Tons became one of Tennessee Ernie Ford’s signature recordings and was later added to the Library of Congress National Recording Registry.
  • It Don’t Mean a Thing (If It Ain’t Got That Swing) helped turn “swing” into one of the defining musical words of the 1930s.
  • Don’t Take Your Guns to Town is one of Johnny Cash’s clearest warning songs, telling a story where bad judgment and pride lead to tragedy.
  • High Hopes turns optimism into a comic lesson, using an ant, a rubber tree plant, and Frank Sinatra’s cheerful delivery to make persistence sound easy.
  • Get a Job by The Silhouettes is one of the bluntest advice songs on the list. No metaphor, no mystery, just employment advice with background vocals.
  • Pack Up Your Troubles in Your Old Kit-Bag became a World War I-era morale song, using cheerful advice as emotional armor.
  • Enjoy Yourself (It’s Later Than You Think) may be one of the most direct old-fashioned advice titles ever written. It is basically a calendar reminder with a melody.

Why Old Advice Songs Still Work

Advice songs still work because people keep needing advice, ignoring it, resenting it, giving it, and eventually realizing someone was probably right. The best advice songs are not just lectures. They use stories, humor, heartbreak, rhythm, and memorable lines to make a lesson stick.

A strong old-fashioned advice playlist should mix Doris Day, Johnny Cash, Tennessee Ernie Ford, Frank Sinatra, Duke Ellington, Bessie Smith, Fred Astaire, Nat King Cole, The Drifters, The Silhouettes, Billie Holiday, and The Carter Family. Some songs offer comfort. Some offer a warning. Some offer common sense. A few mostly prove that people have been making questionable decisions for a very, very long time.

Sources for Advice Songs and Music History

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