No.10 - LL Cool J becomes an author of children's books

In LL’s book, And the Winner Is..., a young basketball player learns the importance of sportsmanship and how to lose gracefully. This advice from a guy who named himself "Ladies Love Cool James," and once rapped: “I'm gonna knock you out / Mama said knock you out.” This hip-hop crossover proves that good intentions don't necessarily make much of a difference.

No.9 - Lil' Romeo markets shoes and snacks

Before becoming a freshman point guard at USC, Lil' Romeo tried to follow in father’s entrepreneurial footsteps. He struck a deal with Keds to make shoes featuring his shirtless picture on top. What parent in their right mind would allow a naked teenage boy’s chest on their daughter’s feet? In 2007, he bought the company Rap Snacks, which makes hip-hop inspired treats like "Yung Joc" Honey Dew Cheese Curls and "Romeo" Back at the Ranch Chips. Snoop Dogg’s stoner image would have been somewhat more appropriate. Needless to say, this hip-hop crossover is no Vitamin Water.

No.8 - Rap Jam: Vol. 1

Despite this 1995 game title’s name, a sequel never made it to stores. For good reason, because it’s a horrible "NBA Jam" rip-off. At first, it seems like a great concept: Play street ball as your favorite rappers. Queen Latifah, LL Cool J, Coolio, Naughty By Nature, Yo-Yo, Public Enemy, Onyx, Warren G and Everlast are all character choices. However, once you choose the character, they look nothing like the celebrity during game play. Not only is there no music from the artists in the game, there is no music at all. It’s just sparse basketball sounds and even sparser cheers from disembodied fans. As hip-hop crossovers go, this one is distinctly lacking in hip-hop.

No.7 - 50 Cent releases Magic Stick condoms

Not satisfied with only his Vitamin Water success (definitely a contender for a “best hip-hop crossovers” list), 50 Cent decided to focus on the other end. He’s teaming with Durex to release his own brand of condoms called Magic Stick. First, what guy would want to be thinking of 50 Cent’s grill when he’s about to have sex? Second, why couldn’t they have thought of a better brand slogan than “BYOP”?

No.6 - Method Man and Red Man in Method & Red

What happens when a streetwise rapper moves to an upscale white neighborhood? You get Fresh Prince of Bel-Air. But what if two streetwise rappers move to an upscale white neighborhood? It gets canceled after nine episodes. Method Man, who was the writer, producer and creator of the series, blamed its failure on the bad editing and laugh track FOX put in. Of course, it couldn’t be the overacting or cheesy jokes that centered around the premise: “Did you know white people are different than black people?”

No.5 - Ice Cube does it all in The Players Club

In 1998, Ice Cube decided he needed a larger role in movie production. So he decided to write, direct, produce, and star in The Players Club. He also produced the soundtrack and wrote many of the songs. Surprisingly, he wasn’t the key grip. All his hard work won a 21% on Described as Showgirls in the hood, the film’s message is summed up by the line: “Make the money. Don't let the money make you.” Yo Cube, “My jimmy runs deep so deep so deep/Put her butt to sleep,” is way catchier.

No.4 - Nelly mixes up some Pimp Juice Energy Drink

Despite Pimp Juice’s financial success, it’s a laughable hip-hop crossover that tastes like a melted Jolly Rancher. The concept is every bit as ridiculous as "Booty Sweat," the energy drink in Tropic Thunder that lampoons it. Just because Nelly told the public that Pimp Juice has nothing to do with pimps, it still sounds like a Blaxploitation **** title. If AM released Man Juice, would you buy it? No, that sounds disgusting. Something tells me Nelly laughs every time he sees someone drinking his juice.

No.3 - The Fat Boys' film career

Hollywood asked: “What else can we do with the joke group, The Fat Boys?" The answer they came up with was a work of cinematic brilliance about hospital orderlies called Disorderlies. Their acting turned out to be slower and sloppier than their rapping. After that, they recorded a goofy theme song for Nightmare on Elm Street 4. The music video gave them yet another showcase for their “hilarious” comedic acting chops. Keep an eye out for a comeback -- their website reports that they’re planning a reality TV show in search of a new member to replace 450-pound Buff Love, who died of a heart attack at 28 years old.

No.2 - Ice-T in Leprechaun in the Hood

Everything from the premise to the name of Ice-T’s character, Mack Daddy O'Nassas, is horrible. The producers just shrugged and allowed their applied their lowest expectations for what the public wants to see, and the result was one of the worst hip-hop crossovers ever seen on film. Ice-T gets to utter such unforgivably bad lines as: “I hope you had sex last night, ’cause I’m gonna come over there and I’m gonna cut off your ****.” The saddest thing isn’t the movie, it’s that it made enough money to warrant a 2003 sequel, Leprechaun: Back 2 tha Hood.

No.1 - Vanilla Ice crossing over into anything

In 1990, Ice released a hit album. Fast forward almost 20 years, and he just did a big show with MC Hammer. Not bad for a has-been! Unfortunately, Rob Van Winkle fails at anything else: Acting in the movie Cool As Ice, recording rap metal, racing motorcycles and wave runners, being a reality TV star, or just being a guest on a talk show. When asked (jokingly!) to destroy the master copy of “Ice Ice Baby” when he was a guest on MTV’s The John Stewart Show in 1999, Ice went crazy and destroyed the set instead. That was just a preview to his role on The Surreal Life, where he held Gary Coleman over a deep fryer and later trashed the house during an angry hissy fit.