Conrad Hilton, the hotel heir whose famous siblings include Paris and Nicky Hilton, just can’t seem to stay out of trouble.

On Wednesday, he made headlines for loosing control and making gestures caught on camera in court during his arraignment. TMZ reports he uttered that the goings on in court were “So f–king gay,” but his words were not picked up by the microphone.

His latest court appearance in connection to claims he violated a restraining order his ex-girlfriend has against him by trying to break into her home.

In this most recent case, Hilton is being represented by Robert Shapiro, the famous lawyer involved with O.J. Simpson case.

Hilton chose not to enter a plea and was released on $90,000 bail and ordered to report to a hospital in Texas.

This is far from the famous heir’s first brush with the law.

Here are some of the most-disturbing Conrad Hilton headlines through the years:

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