If you bet the two-spot under on how many Super Bowl XXXVII ads were directed by Hungry Man’s Bryan Buckley, you would have lost your money. The third Buckley commercial to air in ABC's 2003 broadcast alone (see also Pepsi's "Osbournes" and FedEx's "Desert Island"), this ad via Interpublic Group of Companies' Campbell Mithun in Minneapolis features tax-dodging marijuana enthusiast and legendary country singer-songwriter Willie Nelson in a bit that sends up the Red Headed Stranger’s scofflaw ways.

Designed to remind citizens that even a revered icon like Nelson isn’t immune to the pitfalls of lousy financial planning, “Willie” was only the second time the Kansas City-based company bought time in the Big Game. In 2002 Block hired the Coen brothers to spread the news that Block was expanding into mortgage services. Willie Nelson returned with Block in 2004 as in the form of a doll that offered horrible advice to luckless taxpayers ("Willie Doll").

By the following decade, however, tax prep was more often represented in the Super Bowl by TurboTax ("Love Hurts," "Boston Tea Party" and, in another meta ad about endorsements, "Never a Sellout").

BRAND: H&R Block

YEAR: 2003

AGENCY: Campbell Mithun

SUPERBOWL: XXXVII