The headline to this story practically writes itself, which makes it hard to pick just one. To sum up the latest celebrity financial foible, here are three other titles that didn't quite make the cut:

  • IRS Bites Dogg
  • Uncle Sam Takes On the Doggfather
  • IRS Snoops Around Rapper's Finances

Now, the Snoop scoop: The Internal Revenue Service has filed a $598,309 lien against Snoop Dogg for back taxes owed, according to The Detroit News.

Snoop (a.k.a. Calvin Broadus) is an accomplished rap star (a leader in the "gangsta" oeuvre), gifted actor (consider his nuanced performance as Huggy Bear in Starsky & Hutch), and impassioned environmentalist (his name is synonymous with marijuana advocacy).

Oh, and he's a repeat offender: Last April, the state of California put a tax lien on Dogg's home for failing to pay $284,053 he owed.

That's pretty much all we know at the moment, since Snoop's publicist is keeping mum and the IRS bafflingly does not Tweet about its dealings. We do know that Mr. Dogg is not the only celebrity to fail to file his Form 1040-EZ by the deadline.

IRS Goes After [Insert Celebrity Name]
 "Oops, honey, I forgot to pay our taxes …  again," has become standard breakfast-time banter in households located in certain gilded zip codes. Here are just a few of the highly Google-able individuals carrying around IOUs to the IRS and/or various state tax authorities:

  • Broncos legend John Elway ($5,886)
  • Academy Award-nominated actor Terrence Howard ($1.1 million)
  • Hip-hop singer/actress Eve ($357,000)
  • Retired Oakland A Jose Canseco ($320,000)
  • '80s R&B sensation El DeBarge ($354,000)

And those are just the folks reported so far this month.

What's the deal with celebrities and big tax tabs?
How exactly do the rich and famous manage to so badly botch their finances? In most cases, we can only speculate. Did "pay taxes" not make it onto the April "to do" list? Do they assume someone in their entourage is taking care of business? Did they misplace their tax paperwork in one of their six homes? Do they have liquidity issues, with all their money tied up in castles and dinosaur fossils?

Don't these people have people for these kinds of things?

Actually, we can answer that last one: Yes, they do have people. Sadly, those people don't always have their back.

Nicolas Cage had a guy to manage his affairs. Last November, Cage sued that guy for mismanaging his finances, leaving the actor with $6 million-plus in tax liabilities.

Steven Spielberg, Kevin Bacon, and Kyra Sedwick also had a guy. His name was Bernie Madoff.

Not all financial pros mess up their high-profile clients' finances. When her handlers brought in a guy to help Britney Spears deal with her spendaholism, she learned to live on a monthly budget of "just" $1 million. (Hey, that's one-fifth of what it was previously.) Michael Jackson left a money mess in his wake. But the guy he hired to write his will and set up a trust did a bang-up job, saving his family from ugly courtroom showdowns and helping his lawyers usher his estate through probate.

Today's "teaching moment"
What can we learn from Snoop Dogg's headline-grabbing money troubles? Plenty.

  • Stay on top of your taxes: Get organized and stay organized. And for heaven's sake, mark the due date for filing your taxes on your calendar. In pen.
  • Check out the help's background: Here's how to find a tax pro in the know.
  • Double-check your homework: Even if you hire someone else to prepare your taxes, in the end, it's your signature on the line, and you are solely responsible for paying the consequences of any mistakes. You can audit-proof your own tax return by double-checking the things that trigger the IRS's attention.
  • Never ignore the IRS: If worse comes to worse and you do get a nastygram from the IRS, don't panic. Instead, prepare. Here's a rundown of things that will help you survive an IRS audit.

Dayana Yochim is not afraid to admit that her first exposure to rap was Adam Ant's "Ant Rap." Since then, she has expanded her rap music collection to include actual rap music. The Fool's disclosure policy is way too into world music.