Larry Birkhead has his sights set on a new out-of-control bad girl.

The former boyfriend of the late Anna Nicole Smith is reportedly looking to woo the erratic signer Britney Spears because he is attracted to her.

Howard K. Stern has long been depicted in the media as a money hungry bad guy.

However the one-time companion of the late Anna Nicole Smith says that he does not have the bank balance to back up the claims against him.

Anna Nicole Smith's former lawyer Howard K. Stern has filed a $60 million libel lawsuit against the author who claims Larry Birkhead was his lover.

Stern is demanding $10 million in compensatory damages and $50 million in punitive damages from Rita Cosby, the author of "Blonde Ambition: The Untold Story Behind Anna Nicole Smith's Death" and her publisher Hachette Book Group USA Inc.