It seems odd we'd ever find occasion to offer the following advice: Don't do what Willie did. But as tax day approaches, it's the wisest advice we can offer.
Don't leave the management of your finances to Price Waterhouse, if they turn around and advise you to utilize shady tax shelters. That's what happened to Willie when back in 1990, the IRS seized most of his assets, claiming he owned $32 million in back taxes, penalties, and interest. Yowza.
You don't have enough money to ever contract with a big accounting firm, and the only shelter you know about is the one you can barely afford to keep over your head? That's cool; file your taxes on time to avoid penalties, and try to be chill like Willie. Things'll turn out alright. Here's a soundtrack to ease your filing woes.
10. Johnny Paycheck - "Me and the IRS" (1978)
Take this 1040 and shove it. Paycheck himself filed for bankruptcy in 1990 after running into his own problems with the IRS. Notable lyric: How can I keep my arm around my woman, with Uncle Sam's hand in my pants? If I can't pay the fiddler, well, how the hell am I gonna dance? I don't mind kickin' in my fair share, I might even back up and say yes. But the big man plays while the little man pays, so the hell with the IRS.
9. Johnny Cash - "After Taxes" (1978)
Did Johnny Cash have any problems with the IRS? Hmm, not that we know of. And he also never went to prison, except to perform. It was Merle Haggard who was in prison (and Johnny Paycheck). Notable lyric: There goes that bracelet for her arm. There goes that new fence for my farm. There goes that brand new Pontiac. There goes the shirt right off my back. You can dream about a honeymoon for two, you can dream but that's about all you can do. 'Cause by the time old Uncle Sam gets through, you can buy her a pair of hose, a little powder for her nose, and take her down to Sloppy Joe's for beer and stew. Them are the facts after tax.
8. Willie Nelson - "Who'll Buy My Memories" (1992)
This is the title track from Nelson's The IRS Tapes, an album featuring Nelson solo with his guitar that was released in 1992 to help pay for his debt to the IRS. Want to see some of the rest of what the IRS seized back in 1990, before he was able to pay? Friends of Willie's were able to purchase some of his more personal and sentimental items -- instruments, gold and platinum records, and the like -- many of which are now on display at the Willie Nelson and Friends Museum and General Store in Nashville.
And in a nod to his longtime support for family farms, farmers from all across the country showed up to the government auction of his ranch, making speeches on Willie's behalf and urging the crowd to boycott the bidding. Ultimately, a family farm lobbying group bought the ranch in order to hold it for Nelson. As for his famous guitar, Trigger? He hid it at his manager's house for safekeeping until the whole thing had blown over. Notable lyric: There were the smiles before the tears, and with the smiles some better years. Who'll buy my memories of things that used to be.
7. Sleepy LaBeef - "There Ain't Much After Taxes" (1976)
This lesser-known Arkansas-born rockabilly and country musician recorded with Sun in the '70s, and also had a bone to pick with the IRS. "Great, but what's the deal with his name?" you ask. Well, he always looked like he was about to take a nap. Seriously. Google him. Call them bedroom eyes, call them narcolepsy eyes... he's Sleepy. Notable lyric: Take the taxes from the dollar that is hardly worth a dime; ninety cents is Uncle Sam's, ten cents is mine.
6. Hank Penny - "Taxes, Taxes"
A purveyor of Western swing and a jazz aficionado, Hank Penny also doesn't really like taxes all that well -- surprise! -- but his song's delivery remains upbeat. Notable lyric: Taxes, taxes you will always haunt me. Will I always have to work in vain? You have caused me many tribulations. Taxes, taxes, you have taxed my brain.
5. Little Jimmy Dickens - "(I Got) A Hole in My Pocket" (1958)
Sure, Jimmy. Blame it on the hole. Little Jimmy Dickens likes to refer to himself onstage at the Opry as "Little Jimmy Dickens, or Willie Nelson After Taxes." Notable lyric: I got a hole in my pocket and my money just runs on through. Can't seem to save a dollar like my baby dolly wants me to.
4. Henson Cargill - "Skip a Rope" (1967)
Another lesser-known country singer, Henson Cargill was working as a deputy sheriff in Oklahoma in his early days as a musician, no doubt giving him fodder for this socially conscious 1967 tune, bemoaning everything from verbal abuse and racism to tax evasion. Notable lyric: Cheat on your taxes, don't be a fool. Now what was that they said about a golden rule?
3. Randy Travis - "Reasons I Cheat" (1986)
How about #1: So I'm not so poor. Oh wait. This song's about another kind of cheating, and besides, most people who cheat on their taxes aren't poor. The reason they cheat is that they can get away with it. Notable lyric: A working day too long when everything goes wrong, and a boss who don't know I'm alive. I once had a notion I'd get that promotion, but now I barely survive.
2. Webb Pierce - "In the Jailhouse Now" (1955)
Oh, but sometimes they get caught, and they get sent to the jailhouse! Welcome back to society, Wesley Snipes. Notable lyric: Well I had a friend named Rambling Bob, who used to steal, gamble, and rob. He thought he was the smartest guy in town. But I found out last Monday that Bob got locked up Sunday. They got him in the jailhouse way downtown.
1. Merle Haggard - "Big City" (1982)
Or how 'bout you just walk away, move under the radar, go off the grid, you know. In Montana or wherever it is that people can do that. Notable lyric: Been working every day since I was twenty. Haven't got a thing to show for anything I've done. There's folks who never work, and they've got plenty. Think it's time some guys like me had some fun.
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