Gallery: 20 Celebrity Footwear Fails

When: Summer of 1939
Complex Says: "Clearly, you don't have to be an idiot to be a footwear victim. As the story goes, poor Al was innocently in the market for a sundial. However, a shop owner in Long Island, NY misunderstood his German accent to be requesting 'sandals.' Furthermore and unfortunately, all the shop had was a women's size 11 and instead of rejecting the emphatic salesman, Albert graciously went through with the purchase. The result? Beachside fail."

When: May 1999
Complex Says: "Think about what makes a punchline really, really good; a punchline elicits a facepalm when it's both funny and TRUE. Lloyd Banks' 'Victory' is a classic. The No Limit x Converse MP? Not so much — despite Master P being a legend. And by the way, if anyone can give us the scoop on where we can get that jersey, let us know ASAP!"

When: August 2002
Complex Says: "Before he was getting invited to perform in Paris for the release of the Quai 54, Fab was known by many as the 'Variant King.' Not only did Bobbito García expose some of Fab's sneaker shortcomings via ESPN's 'It's The Shoes', but Fab also revealed a pair of faux French Blues (peep the white in the tongue) in his video alongside Jagged Edge. Trade it all? Nah, bruh, you can keep those!"

When: August 2003
Complex Says: "In 1997, Yukmouth was indirectly and insubstantially nominated for a Grammy for a song entitled 'Stomp' — which begs the question: How authoritatively can one actually stomp in fake Jordan XVIIIs?"

When: February 2004
Complex Says: "In the late 1980s, James Gragg of Tulsa, Oklahoma conceived and invented the first 'original free-spinning spinner.' Twenty years and thousands of patent infringement cases later, Davin Wheels of Milwaukee — unable to get a booth at the LA Auto Show — joined with another vendor, Latrell Sprewell's (also coincidentally from Milwaukee) Sprewell Racing, to display their 'continuous motion wheel.' The rest, that's history. Divine Intervention? Probably not. An amazing footwear fail? Without a doubt."

When: May 2004
Complex Says: "Although you may have seen a friend, acquaintance or stranger fail in these bad boys, that person was certainly not Bryan Williams. For him, fly is more than just kicks — it's a way of life. Rock Lugz, travel in a G5. Bet $2 milli on the Miami Heat, party with Mark Cuban. Get where we're going with this?"

When: April 2007
Complex Says: "So you bought some faulty kicks — it's okay, no one will ever know. Unless you wear them in a photo shoot and subsequently use those photos for your album art. We'd be covering our faces in disgust, too!"

When: June 2007
Complex Says: "We get it, Puff has a lot of money and he deservedly likes to flaunt it. However, c'mon, Diddy... 18k gold laces? The sneaker company's name is 'Upper Echelon Sneakers' — that's a fail in and of itself."

When: November 2007
Complex Says: "One would think that Nas would look a little less disgruntled while undertaking an endorsment for the 310 Motoring 'Disciple'. But, by the looks of things, we can see why he'd be unhappy."

When: January 2008
Complex Says: "After performing 'Halle Berry' for Congress and becoming a spokesman for the FILA Helmsman, it's pretty clear that Hurricane Chris' career has taken a pretty steep hit — we guess it's safe to say that FEMA won't respond to relieve this hurricane, either."

When: February 2008
Complex Says: "Candy Apples aren't usually associated with the 'scary' part of Halloween, but it looks as though we can thank Yums and Soulja Boy for drawing that connection."

When: March 2008
Complex Says: "If you stick to what Jordan releases, hardly ever can you be led astray. Buuut, when you start messing with all kinds of crazy fakes and whatnot, you certainly look corny and definitely place yourself in the fail category."

When: December 2008
Complex Says: "Although Drake has stepped his sneaker game up as of late, it's still always good to be reminded of where you came from. There's been a lot of back and forth as to whether these are custom or fake but considering the point in his career and how crazy these look, they were definitely a rookie mistake."

When: June 2009
Complex Says: "In one of the most talked about sneaker bungles in the history of mankind, our buddy Big Boi let his guard down to online sneaker imposters. Being an honest guy, Big Boi subsequently exclaimed, 'They got me... I paid $500 a piece for about four pair.' Additionally, the worst thing about the whole situation was that ol' Antwan rocked these crazy VIIIs while performing at Sneaker Pimps and CNN later ran a story lauding him on his sneaker prowess. It's all good, though — honest mistake!"

When: December 2009
Complex Says: "In defending his wedding day ensemble, The-Dream stated that he is 'kinda cultural' and that 'In history, once it goes back, somebody will look back and say, 'Oh, that was hot.'' Well, it's only been two years, so history probably hasn't 'gone back' enough, but Dream does look a little like G-Dub — that's kinda cool, maybe that's what he was talking about?"

When: January 2010
Complex Says: "Though we'd be hard-pressed to say that CB never let us down, sartorially, we still rock with Chris most of the time when it comes to his kicks. Buuut, when Chris Brown goes and gets all Peter Pan on us, that's when we start to lose our faith again."

When: April 2010
Complex Says: "Known for his roles in 'Step Up' and 'Dear John', Channing Tatum has developed a name for himself as a softey-breakdancer. Now, it looks as though dress code violator should be added to the list, because the Vibram FiveFingers are a total no-go."

When: October 2010
Complex Says: "Karl Malone will always be one of the greatest frontcourt players of all-time — it's just sad that our last vision of him had to involve Shape-Ups."

When: March 2011
Complex Says: "When we're talking fly, HOV is usually in his own lane. However, when Jay declared lift off in these radii Moon Walkers, his altitude dropped down way below sea level. It's okay, though, 'Watch The Throne' is easily one of the best ways to save face."

When: April 2011
Complex Says: "This ain't nothin' new to Clyde, stunting is a HABIT. While we're trying to figure out whether the boots were a fail or not, Walt's countenance reads "It's already 9:30PM, but I've got thousands of next year's swatches to go through back at the penthouse."