By Margaret Lyons
January 06, 2011 at 06:17 PM EST

O Captain, my captain. Or should that be Cap’n? Yes, the highly decorated military mascots are facing off in this round of the Big Shill Bracket Game, which celebrates the best advertising icons in pop culture. In this round, it’s rum vs. another sugar-based treat, plus scrawny white dudes: Mac Guy Justin Long, back when he was just semi-famous and the incessantly melodic Free Credit Report guy. But don’t leave out beloved biological wonder Grimace, the physical embodiment of loving milkshakes, or the similarly rotund but perhaps less jolly Michelin Man. Finally, are they always after your Lucky Charms, or do they just keep going and going and going? Check out the entire bracket here, and then cast your votes!

CAP’N CRUNCH

Product: Cap’n Crunch cereal

Debut year: 1963

Catchphrase: Crunchatize Me, Cap’n!

Claim to fame: Battling soggies, of course. Well, that and making sure kids loved the entire line of Cap’n cereals.

Strength: Sugar highs.

Weakness: Well, that apostrophe isn’t doing anyone any favors… and neither is the crummy nutrition…

CAPTAIN MORGAN

Product: Captain Morgan Run

Debut year: 1944

Catchphrase: N/A

Claim to fame: Is being a historical privateer not enough? If not, then the one-leg-on-a-barrel thing.

Strength: Rum goggles.

Weakness: Even though he’s been on rum bottles for decades, he hasn’t had much of a television presence until more recently.

MAC GUY

Product: Apple computers

Debut year: 2006

Catchphrase: “I’m a Mac”

Claim to fame: Along with John Hodgman, introducing the world to computerized personhood. Also, it’s Justin Long.

Strength: Drew Barrymore’s endorsement.

Weakness: People are way, way too used to using Windows.

FREE CREDIT REPORT.COM GUY

Product: Freecreditreport.com

Debut year: 2008

Catchphrase:: “Freeeee credit report dot coooom!”

Claim to fame: Catchy jingles. Many, many jingles.

Strength: Melodic abilities, a seemingly supportive band, and a truly staggering ability to get songs stuck in our heads.

Weakness: Well, he’s broke as a joke.

GRIMACE

Product: McDonald’s

Debut year: 1971, with a revamp in 1974

Catchphrase: N/A

Claim to fame: Before there was Shrek, America’s favorite giggle ogre-ish biological anomaly was the fuzzy purple Grimace. Hamburglar might have all the guts, but Grimace gets all the glory.

Strength: Can anyone even remember the name of the chicken girl thing? No. But who doesn’t love Grimace? And shakes?

Weakness: He started out as “Evil” and had to be rebranded.

MICHELIN MAN

Product: Michelin tires

Debut year: 1894. Wow!

Catchphrase: N/A

Claim to fame: Step aside, Pillsbury Dough Boy. The Michelin Man — proper name “Bibendum” — is the iconic representation of all things obese and cuddly .

Strength: Spare tires.

Weakness: Spare… tires…

LUCKY THE LEPRECHAUN

Product: Lucky Charms

Debut year: 1963

Catchphrase: “They’re always after me Lucky Charms!” and “They’re magically delicious!”

Claim to fame: Somehow, Lucky makes crunchy, nasty, shriveled, colored marshmallows actually sound enticing.

Strength: Even among the cereal mascots, Lucky is maybe the most iconic of them all.

Weakness: Hey, a racist caricature.

THE ENERGIZER BUNNY

Product: Energizer batteries

Debut year: 1988

Catchphrase: They keep going and going…

Claim to fame: How many times did viewers get tricked into thinking they were watching some commercial, just to have the Energizer Bunny shuffle his way on screen, pounding his wee bunny drum, to the dulcet tones of “stiiiill going!”? Many, many times.

Strength: Endurance, of course.

Weakness: Flip-flops.

Okay, PopWatchers, let’s hear it: Whose shilling gets top billing?

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