From Plato to the IRS: The tax joke is on us

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I love April, but as a self-employed writer, I’m knee-deep in tax receipts and spreadsheet misery.

I love to hear what our great minds have said about their own tax miseries:

“We contend that for a nation to try to tax itself into prosperity is like a man standing in a bucket and trying to lift himself up by the handle.” — Winston Churchill

“I don’t know if I can live on my income or not — the government won’t let me try it.” — Bob Thaves

“They can’t collect legal taxes from illegal money.” — Al Capone

Hey, Al, you make me want to get into the bookie business.

Here are more gems:

“The hardest thing in the world to understand is the income tax.” — Albert Einstein

“Today, it takes more brains and effort to make out the income tax form than it does to make the income.” — Alfred E. Neuman

“A fine is a tax for doing something wrong. A tax is a fine for doing something right.” — Anonymous

You got that right, Anonymous. The more we make, the more our silent partner, the government, takes.

Here’s more on tax pain:

“You don’t pay taxes. They take taxes.” — Chris Rock

“Collecting more taxes than is absolutely necessary is legalized robbery.” — Calvin Coolidge

“It’s income tax time again, Americans: time to gather up those receipts, get out those forms, sharpen up that pencil, and stab yourself in the aorta.” — Dave Barry

Dave, I wish you were still writing your hilarious column — especially during tax time.

Here’s more tax sense:

“America is a land of taxation that was founded to avoid taxation.” — Laurence J. Peter

“What the government gives it must first take away.” — John S. Coleman

“Congress can raise taxes because it can persuade a sizable fraction of the populace that somebody else will pay.” — Milton Friedman

Hey, Milton, somebody needs to explain that fiction to New York City voters.

And more:

“A tax loophole is something that benefits the other guy. If it benefits you, it is tax reform.” — Russell B. Long

“I am proud to be paying taxes in the United States. The only thing is I could be just as proud for half the money.” — Arthur Godfrey

“Taxation with representation ain’t so hot, either.” — Gerald Barzan

Believe it or not, the IRS used to publish these humorous tax quotes on its website:

“People who complain about taxes can be divided into two classes: men and women.” — Unknown

“The income tax has made more liars out of the American people than golf.” — Will Rogers

“Where there is an income tax, the just man will pay more and the unjust less on the same amount of income.” — Plato

Well, then, Plato, I guess tax woes have been around for a while.

As I prepare endless tax details for my CPA, at least I can find joy in these great quotes:

“A fool and his money are soon parted. The rest of us wait for tax time.” — Unknown

“Did you ever notice that when you put the words ‘the’ and ‘IRS’ together, it spells ‘THEIRS’?” — Unknown

“The wages of sin are death, but after they take the taxes out, it’s more like a tired feeling.” — Paula Poundstone

Copyright 2026 Tom Purcell, distributed exclusively by Cagle Cartoons newspaper syndicate.

See Tom Purcell’s syndicated column, humor books and funny videos featuring his dog, Thurber, at TomPurcell.com. Email him at [email protected].

Find Tom Purcell’s syndicated column, humor books and funny videos of his dog, Thurber, at TomPurcell.com. Email him at [email protected].