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Iconic bad boys come in all shapes and sizes and so do the houses that they once lived in. Currently the real estate market is proliferated with homes from some of the most infamous men out there. Those seeking to up their street cred should consider buying (or renting) the homes of some legendary bad boys who have many millions in publishing, fashion and the music industry. While the price tags of the homes may require jumbo mortgages to finance, because of the fame associated with the properties, chances are they will move quickly.

Hugh Hefner's Playboy Mansion, Chicago, Illinois

Hugh Hefner is the world's first authentic ladies man as he built a publishing empire off of barely clad ladies, and subsequently reaped the rewards in the form of money and more chicks than he could possibly handle. Before Hef purchased the current sprawling Playboy Mansion located in Los Angeles, California in 1971, the Playboy king had his home base in Chicago, Illinois. A part of the original Playboy Mansion (which has been converted into individual apartment units) is currently for sale for a measly $2.75 million.

The French brick and limestone Chicago mansion was originally constructed in 1899 at 1340 North State Parkway. The property originally featured 72 rooms and was a Mecca of decadence from 1959 until 1974 (when Hef relocated to LA for good). When the property first flipped it was purchased by the Art Institute of Chicago for student housing. During the 90s, the mansion was renovated and subdivided into seven luxury condos. The 3,900 square foot first floor unit featuring, 3 bedrooms and 3.5 baths is currently for sale. The current price features a 9 percent reduction off of the original listing price of $2.9 million. The current owner slashed the price like so many other Americans struggling to sell their homes in the unsteady economy.

Christian Audigier's Home, Hancock Park, California

Designer Christian Audigier built his fortune by making embellished, tattoo styled t-shirts the "it" wear for gentlemen wishing to stand out of a crowd. Audigier is a French born designer who worked his magic on iconic brands including Lee, Liberto, Kookai, Von Dutch, Naf Naf and bad boy favorite Ed Hardy. While some critics have cited his designs as flashy and tacky, those words have not deterred fans from buying his line and feeding his fortune.

Audigier's seven-bedroom, seven-bathroom tuft house in tony Hancock Park, California is currently for sale with a listing price of $8.299 million. The photos appearing on the local multiple listings service shows that the home is as bedazzled as his line of t-shirts. The property is fully gated, provides a complimentary Rolls Royce Phantom 5 as a free gift with purchase, swimming pool and an outdoor living space complete with a kitchen.

R. Kelly's Rental Pad, Chicago, Illinois

Just because R. Kelly is a top selling R and B artist does not mean that he has mastered the art of the local Chicago, Illinois real estate market. Earlier this year the pop star listed his home for a whopping $3.89 million sales price, but like many other celebrities adjustments had to be made based on current market conditions. The property has been pulled from the sales market and has been converted to a rental property with a monthly payment of $35,000.

The home was previously a church and now features 5 bedrooms, 4.5 bathrooms, indoor lap pool, 1,600-gallon shark tank and 1,500-square-foot rooftop terrace. Like many luxury properties offering free gifts with home purchase, this rental provides complimentary cleaning, personal chef and masseuse services for one month. Those torn between renting and buying the home can speak with the real estate agent directly to see if purchasing the property is still an option.

Even though all the bad boy properties require jumbo loans to finance the purchase, now is the time for consumers to jump at the opportunities offered by the luxury home markets. Even within the jumbo mortgage market, mortgage rates are at historic lows making it less expensive to borrow the money needed to finance a home purchase. Plus, many owners are anxious to sell their large homes, so discounts abound.