10 Celebs That Totally Win at Life and at Halloween


While it’s true that celebrities have a lot more cash to spend on their Halloween costumes than the rest of us (and their personal stylist is just a phone call away), that doesn’t automatically mean their costumes are ten times better than the average mortal. In the end, it’s all about creativity and the ability to not take yourself too seriously. So Hollywood stars with a limited imagination, no matter how much cash they spend, will be just as much a walking cliché as everyone else you see dressed up as the Gangnam Style guy.

Clothes maketh man, and that includes your ridiculous Halloween outfit. It definitely tells you something about someone’s personality, creativity and sense of humor. So, when you win at Halloween, you usually win at life too. Here’s a few celebs who aren’t afraid to fly their freak flag, make fun of themselves and show off their creativity. And they’re just plain awesome in general too, proving that when you win at Halloween, you win at life in general.

#10 – Heidi Klum

Yup, you’re actually looking at supermodel Heidi Klum. And no, it’s not a picture of her without any make-up, this is one of her many ridiculously awesome Halloween outfits. Every year, she goes out of her way to come up with the most insanely creative outfit out there. She has been dressing up as the Hindu deity Shiva, a giant bird, a monkey and as a skinless woman.

And she wins at life too, for example saving her own kids from drowning in the ocean when they were caught in a riptide. She swam out, saved her kids and then she swam back, because the two nannies needed saving too. She really puts the super in supermodel. And if there’s an award for weird lucky charms, she’ll win that too, because she carries all of her baby teeth around in a pouch, everywhere she goes.

#9 – Ellen Degeneres

And the award for looking surprisingly and eerily similar to Nicki Minaj goes to… Ellen Degeneres. Her outfit came complete with fake boobs, fake ass, a blonde wig and the exact same outfit Nicki Minaj wore when she was on Ellen’s talk show. Some other weird and winning outfits of hers, include dressing up as a wedding album and a life size edition of Oprah’s magazine.

She’s funny as hell, even voted funniest person in America in 1982. But she’s also a prominent gay rights activist and not just that, she’s actively involved in a lot of humanitarian projects. For example, she was named special envoy by Hillary Clinton for Global AIDS Awareness. Ellen is also a big fan of turkey. Not eating them though, but rather adopting a few for Thanksgiving, so fewer people will eat a traditional turkey dinner.

#8 – Cindy Crawford

This photo may suggest that Slash and Axl Rose have finally settled their two decade long feud and are in the process of getting the band back together. But this Slash is none other than former supermodel Cindy Crawford, holding an air guitar. Many people have dressed up like Slash, but she’s doing a pretty bang up job. Especially because of her matching husband, who really looks the part.

Cindy Crawford was the first supermodel to ever pose for Playboy. She got a lot of guff from feminists everywhere, but she just responded: “I thought the whole point of feminism was that it is all about making your own choices.” She’s also very actively involved in charity (especially for children’s leukemia, to which she has lost her brother) and is a vocal supporter of gay rights.

#7 – Deryck Whibley

You’re picking your Halloween costume and you want to go with a monster theme. But the only real monster you can think of is, your famous ex-wife. Sum 41 band member Deryck Whibley decided to just go for it and his famous ex is Avril Lavigne. He put on the quintessential hoodie, put on some heavy eyeliner and wore a blonde wig with a green streak.

Call it tasteless if you want, you can’t deny the fact that it’s creative, especially when your current girlfriend dresses up as current husband and universally hated rocker Chad Kroeger, from Nickelback.Chad didn’t like it of course, but then again, he has to deal with ridicule on a daily basis. He tweeted a not so witty comeback: “Great costume. We wanted to dress up like you guys, but all the parties had celebrity themes.” Oh, snap.

#6 – Seal

Seal, the singer, not the animal, is the shiny metal guy on the right. Up until their divorce, he just about rocked every Halloween party with Heidi Klum. The two literally spent months planning and working out some of the craziest costumes out there. And this metal outfit is certainly the British singer’s best one.

Seal is best known for his monster hit song Kiss from a Rose (also the Batman Forever soundtrack) and the scars on his face, which were rumoured to be the result of child abuse, but were actually caused by a rare skin disorder. Seal’s also a hopeless romantic. He built a Quinzhee (a sort of igloo) on a glacier and proposed to Heidi Klum in it. The couple also renewed their marriage vows every year and Seal never hesitated to adopt Klum’s daughter as his own.

#5 – Beyoncé

Lovingly nicknamed Queen Bee, Beyoncé turned that into both outfit and pun and sporting a great pair of legs while at it. It may not be the most extravagant outfit out there, or even the most creative, but, looking like she does, all is forgiven and forgotten.

But it ain’t looks alone that make Lady Beyoncé a winner. She holds the record for most Grammys won in one single night and was voted the 4th most powerful celebrity by Forbes in 2008. If they teach a course about you in Harvard Business School, with a case study called The Business of Being Beyoncé, you must be doing something right. If you’re lauded as a feminist role model and your enormous success is considered worthy of academic research, you pretty much are the textbook example of winning.

#4 – Will Ferrell

Professional funnyman Will Ferrell doesn’t need Halloween as an excuse to dress up in ridiculous outfits (the movie Zoolander being a very good example). But hey, when it does turn out to be Halloween, why not dress up as the super intelligent 3D-animated alien superhero Megamind? He already did the voice, so no one could be more convincing.

But what makes Will Ferrell a real winner for one is filming his 3 year-old daughter very eloquently berating and evicting him, while playing the part of a stone cold landlady with a drinking problem. And secondly, not hesitating for a second to fly over to the set of Kingpin for an uncredited cameo and no camera time. During the final scene of the movie, you hear a guy shouting the words “Ernie, you’re the man!” That would be Will Ferrell.

#3 – Neil Patrick Harris

Check out this legen… wait for it… dary outfit by the guy who defines gentlemanlike coolness. Neil and his family dress up in perfect thematic unity every year. Whether it’s a Gotham theme, Alice in Wonderland, Peter Pan, or just a regular horror theme (miniature bride of Frankenstein included) the whole family rocks it with that famous suave.

And Neil Patrick Harris is just an all round cool guy. For example, he found out he was playing in Harold and Kumar go to White Castle, but no one had bothered to inform him of that or even ask him if he wanted to. His manager advised him to call his lawyers and make it stop, but Harris decided to read the script, thought it was hilarious and decided to be in it anyway. And that movie also landed him a part in How I Met Your Mother.

#2 – Dwayne Johnson

For The Rock, dressing up as the Hulk is pretty easy. He already has the muscles, so all he needed was a wig, ripped jeans and some green paint really. But the result is really awesome nonetheless. And just like the real Hulk, when you’ve seen him wrestle, you wouldn’t like him when he’s angry.

But Dwayne Johnson is more than an incredible walking mass of muscles. He’s actually a very funny guy and loves to poke fun at himself. When people found an awkward early photo of The Rock sporting a fanny pack and a turtleneck, he was the first to suggest it would make a great Halloween costume and shared the best fan photos on his Twitter account.

#1 – Zach Braff

How cool is it to dress up like someone famous for Halloween and then actually meeting that person at a party? It happened to Scrubs star Zach Braff, when he dressed up like 80’s action hero Kurt Russell’s character from the movie Big Trouble in Little China and then just bumped into him. Kurt thought it was pretty cool too.

But Zach doesn’t just win at Halloween. In the show Scrubs, he’s best buddies with Turk, played by Donald Faison. But in real life, they’re best buddies too and their shenanigans are just as funny. In reaction to Indiana’s Religious Freedom Restoration Act, Zach tweeted “If you really and truly want pizza for your gay wedding in Indiana… We will make it for you.”, along with a suggestive photo of the two best buddies in a speedboat.