Rick Calamaro, Charlie Sheen's former longtime personal assistant and close friend, was found dead in his Los Angeles apartment Sunday.

The 46-year-old club promoter had reportedly been dead for a few days when police found him, according to TMZ.

"Numerous pain medications and an open bottle of alcohol" were littered in his apartment, the site reports.

Calamaro was considered one of Sheen's closest friends and was reportedly present during Sheen's infamous 36-hour drug binge in October 2010.

Since then, many have speculated that Calamaro was a bad influence on the troubled actor, and may have even supplied Sheen with drugs over the years.

Calamaro's cause of death has not yet been determined, and the "Anger Management" star has not yet released a statement.