What else is left to do when you’re one of the most wanted criminals in your time who got busted and jailed in the highest security prison? You would use your brainpower and escape in the craziest, most creative way with the help of your accomplices. The options are endless— from underground tunnels to transforming into a woman. Unfortunately, these three criminals did not let the most secure prisons stop them from attempting their most daring escapes.

Ronaldo Silva

After a failed attempt at escaping with the help of armed men invading the jail to break him out, drug trafficker Ronaldo Silva took his escaping game to a different level in 2012 when he decided to disguise himself as a woman. With the help of his wife, who exchanged clothing with him during one of her visits, he dolled himself up by shaving his arms and legs, even putting on lipstick, a lovely curly wig, wearing a bra and panties, and slipping into a blue dress, and wearing high heels.

According to jail director Carlos Welber,

“He was wearing a wig, painted false nails and a long dress. He’d spent a long time shaving his legs and arms. There was a lot of preparation and premeditation involved in this.”