The world lost a comedy legend this week with the passing of Don Rickles, one of the funniest (and meanest) voices ever to take the stage.

Newspapers across the country have done their best to memorialize this larger-than-life entertainer, but we think that should be left to someone who knew him best: Frank Sinatra.

The singer first met Rickles in 1957 and they stayed lifelong friends afterwards. Rickles was famously the only person allowed to joke about Sinatra's fragile ego, and as you can tell from this story he took his job seriously.

Throughout their careers these two icons often appeared together, including at comedy shows where they roasted each other.

Old Blue Eyes even managed to persuade Rickles, a lifelong Democrat, to perform at Ronald Reagan's second inauguration, which is remembered as one of his best routines.

The two were so close that Rickles was even one of the pallbearers at Sinatra's funeral. It's sad to see this legend go, but we bet he's having a lot of fun with Frank up in heaven.

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