Before They Were Famous: The 10 Most Regrettable Celebrity Commercials

Role: The "Cool" Early '90s Teen

Synopsis: Thanks to the infamous "Care Bear Backlash" of the late '80s, by the time 1990 rolled around, anything marketed to kids had to be "edgy." Here, the notoriously family-friendly (read: "square") Nintendo enlists a young Paul Rudd to shake up that wholesome image for their latest product, the "Nintendo Super-Happy, Fun-Time Game Box" (working title).

Bottom Line: Considering Rudd hasn't dropped below four levels of ironic detachment since 1995, his wide-eyed amazement at his surroundings (Trench coats! Smoke machines! SimCity!) seems less than sincere in retrospect. It's not exactly Rudd's fault, either-even to our young, pre-Clueless eyes, this ad stunk of cheese.

Bonus Moment: The cryptic "New Zelda and Football to come" disclaimer at the end of the ad.

Role: Gummy Cheerleader

Synopsis: Meg Ryan's cheerleader friends give her a an old-fashioned razzing over her "fancy" mint-flavored toothpaste, until it is revealed that Meg's good oral hygiene has apparently nabbed her a date with the dreamy Jack Reid. (Not revealed in the commercial: Meg puts out like a wolf in heat.)

Bottom Line: So, girls who use mint toothpaste are easy. Whatever. We still pity an era where women's locker rooms were portrayed as places of sweaters and serious conversations about fluoride, and not the misty, slow-motion fantasies we now know them to actually be.

Bonus Moment: "My dears, this is serious toothpaste." Enough said.

Role: A Radical Dude

Synopsis: Despite the best efforts of Seth Green's haircut, Nerf guns are still pretty much the coolest things, ever.

Bottom Line: This ad makes it scarily apparent that it's now 2007 and Seth Green has not yet hit puberty. Also, from the smokin' fashions to the "NOT!" fake-out, it's a great start to our next article, "Things We Pretend Not To Remember About the Early '90s."

Bonus Moment: Mandatory Kids' Commercial Trope No. 23: Before all's said and done, a representative of the adult world must be taken down in a suitably humiliating fashion. Here, a mime falls into a pond. Man, does Nerf get kids, or what?

Role: Straight-Talking, Streetwise, Vaguely Racist Caricature

Synopsis: Lawdy, mastuh, sho' is hard being a po' ol' telephone repairman. Good thing 'dis mouthwash is such a powerful concoction! Now, who wants some of Aunt Jemima's pancakes?

Bottom Line: So the message is that even if something tastes bad, it can be good for you? We had no idea! Thank goodness Listerine commissioned such an informative and non-condescending minstrel show to get the message across.

Bonus Moment: The other guy's closing non-committal grunt of a response to Freeman's twisted, mouth-cleansing logic.

Role: Embarrassingly Over-Enthusiastic Guy Who Breaks Into Song and Dance

Synopsis: It's a classic commercial set up-this product is so great, that the mere thought of using it causes people to start hollering and gyrating like epileptics. Here, a pre-Moonlighting Willis stars as a good ol' boy who loves his wine coolers so much, that he and his jug band have to start an impromptu porch-front jam session.

Bottom Line: Ignore momentarily that Seagram's prize beverage will be a pop-culture punch line for years to come. Instead, focus on Bruce's slurred, "authentic-drunk" performance, which allows him to deliver the inexplicable tagline "It's wet and it's dry" with complete conviction.

Bonus Moment: If you look closely, tipsy Bruce Willis actually takes a swing at the guitarist 20 seconds in, and then tries to pass it off as a pirouette.