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Top 10 Male Entourages

I once had an entourage. It was myself and my younger friend Gabriel, and we hung out and had crazy times, like this one time when we ate licorice and watched scrambled porn. Wait…that’s not an entourage–that’s just sad.

One of the best parts about being a celebrity must be hanging out with other celebrities. One star gets the royal treatment, but multiple stars bring the galaxy to a halt and allow anything to happen. They can own a city and the hearts of the women inside it, like how the Brat Pack owned L.A., the Rat Pack owned Las Vegas and the Beat Generation owned New York City. This article pays homage to those famous men who ganged up and owned. They’re ranked by their power as a group, and the impressive stories that they inspired.

No. 10 – The “Not On Our Watch” Men

Why are superstars George Clooney, Brad Pitt and Matt Damon so far down on our list? Honestly, because their crew is boring.

Don’t get us wrong; they do great things when they hang out like founding the human rights group Not On Our Watch. However, they don’t seem to generate the crazy stories that other entourages do. When the rumor hit that Pitt and Angelina Jolie would marry at Clooney’s vacation home, George ordered reception tables to mess with the paparazzi. That’s about as crazy as their pranks get, although sometimes they can be pretty witty. Oh, and Pitt and Damon did cameos for Confessions of a Dangerous Mind.

No. 9 – The Brat Pack

One night in 1985, Emilio Estevez, Rob Lowe and Judd Nelson were drinking Coronas and flirting with groupies at the Los Angeles Hard Rock Cafe. Writer David Blum was tagging along and invented the name for the young, high-living circle. Along with the above three, the Pack included Anthony Michael Hall, Andrew McCarthy, James Spader, Robert Downey Jr., and Charlie Sheen (but only because his brother Emilio let him in). They partied hard together and made headlines in doing so. Film director Jay Roach said: “They seemed charmed in the way the Rat Pack seemed charmed.” It didn’t last.

No. 8 – The Hellraisers

Known for their talent and equally tremendous excess, Oliver Reed, Richard Burton, Richard Harris, and Peter O’Toole are forever linked in the memories of the British public. During the ‘60s, this pub-crawling crew became larger than life. Burton and his wife Elizabeth Taylor downed three to four bottles a day, each. Harris drank two bottles of vodka a day while he read in the papers what he’d done the night before. Reed became infamous for drinking “gunk,” an ice bucket with every drink in the bar poured into it. O’Toole fought everyone from paparazzi to cops. Director Peter Medak said: “You didn’t know if they were going to kiss you or punch you right in the face.”

The Top 7 Male Entourages at AskMen.