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Cracker Jack Boy

Originally called “Candied Popcorn and Peanuts”, Cracker Jack was sold at the first Chicago’s World Fair. Not only is it well known for coming with a prize, but it will be forever linked with baseball as sung in “Take Me Out to the Ball Game”.

Vanilla Ice

Try as he might to make a new name for himself, Robert Van Winkle, better known as Vanilla Ice, will always be remembered for such classics as “Ice Ice Baby” and “Ninja Rap.” While the rapper now dresses like a member of Limp Biscuit, it’s his hi-top haircut and harem pants of the ’80s that make his costume fun to imitate.

Flavor Flav

Hip-hop pioneer, Flavor Flav has stayed true to his style despite adding reality television star and restaurateur to his resume. Combining lots of “bling” with a giant clock necklace, copying Flavor’s style probably won’t score you a model like Brigitte Nielsen but it will have people asking you for the time.

Beck

Beck has come a long way since writing songs like “Loser” and “Devil’s Haircut” but oddly enough his fashion sense is still pretty much the same. Pick up a leather jacket and dress pants at the thrift store and you can pass as ’90s or present day Beck. The boombox is optional.

Lisa Loeb

Lisa Loeb became America’s sweetheart when she burst onto the music scene with her song “Stay.” While she may be considered a one-hit wonder to some, her style has managed to stick around. While dressing in all black is simple you really need the tortoise shell cat eye frames to make this look work. Otherwise people might just think you’re a beatnik.

Bad Grandpa Irving Zisman

Jackass presents 86-year old Irving Zisman (Johnny Knoxville). He’s on a cross-country trip with his young grandson Billy, and they’re raising hell all the way. Irving is gonna show all the young’uns what it means to be Bad Grandpa.

2 Broke Girls

In 2 Broke Girls, Max (Kat Dennings) and Caroline (Caroline Channing) are besties who are from opposite side of the tracks. If they’re not baking cupcakes or schmoozing with Martha Stewart, you’ll find them working at the diner, slinging burgers and fries.

Al Bundy

In Married… with Children, Al (Ed O’Neill) is head of the Bundy household. As a high school football player he once scored 4 touchdowns in one game, but he now struggles through his job selling women’s shoes and his hopeless family. Al’s only reprieve is his alone time on the toilet and on the couch watching episodes of Psycho Dad.

Cliff Huxtable

One name is synonymous with ugly sweater: Cosby. On the Cosby Show, Cliff Huxtable (Bill Cosby) immortalized the ugly sweater, taking it beyond anything we’ve seen before or since. The nice thing about these crazy patterns is that no one would ever notice if you got Jell-O pudding on them.

The Red Queen from Once Upon a Time in Wonderland

Not to be confused with The Queen of Hearts, The Red Queen is cool, collected, and ruthlessly evil. Together with Jafar, The Red Queen plots to keep Alice from her true love.

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