‘Entourage’ Creator Doug Ellin Stops By To Talk Charlie Sheen, TruTV, Michigan State’s Tom Izzo, Pickleball And So Much More

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Take the tarp off the black Lincoln, proudly display your Viking Quest memorabilia, que up some Saigon and cruise through OutKick’s version of Hollywood Boulevard. Today’s edition of nightcaps comes with an assist from Doug Ellin, the man who created Entourage.

In the midst of my standard morning routine of 200 pushups, sit-ups and squats, (or is it 300?), I dialed up an old episode of Entourage – something I do with the same regularity as a cap full of Metamucil.

(If you know, you know).

For those of you who somehow skipped last Wednesday’s nightcaps: A) How dare you.  


B) I’m a man, I’m 40! So Metamucil is now as much a part of me as my receding hairline.

That’s my long-winded way of saying an Entourage rewatch, for the umpteenth time, nudged me enough to reach out to Doug Ellin to tag-team this edition of nightcaps. To me, Entourage, which premiered on HBO in 2004, is among the most rewatchable shows of all-time. If you haven’t watched it, get yourself to TruTV sometime soon (they recently purchased the show to run in syndication) or fire up HBOMax. It’s must watch. Ari Gold and Johnny Drama are two of the greatest characters of my lifetime. They’re one Kenny Powers away from forming HBO’s Holy Trinity of comedy.

And if you’re not an Entourage fan, well, grab yourself a seltzer and enjoy the Real Housewives. We’ll try this again next week.

Doug Ellin created “Entourage” and doesn’t envision the show changing much today from when it first aired in 2004. (Photo by Dimitrios Kambouris/WireImage).

Before we tip our glasses, a couple quick notes:

Doug Ellin currently co-hosts one of the biggest podcasts in the country, Victory the Podcast, and is in the process of shopping a new series, Ramble On, which stars Charlie freakin’ Sheen. More on that later.

Some of Doug’s comments have been shortened for time and clarity.

An Entourage Reboot Has Been Rumored For Years

I asked Doug about reviving Entourage – something that’s long been rumored – and how much, if at all, the show would differ because of the world we live in today. To the surprise of few, a bunch of Libs have done their best (unsuccessfully) to cancel Entourage after it went off the air because four male friends joking around is just oh-so offensive.

Doug Ellin:

“I don’t think there’s anything (I’d do) differently. I just think words evolve. Cultures change and there’s things you don’t say anymore. Not because they’re not politically correct. But because you’ve evolved and you’re not an idiot. You can’t walk around an office the way Ari [Gold] used to. And by the way, there’s people who will try, but someone will film you and you’ll lose your job. It’s just that simple. While Entourage was a wish fulfilment comedy, it was (also) a very real look at Hollywood back in 2003.It wasn’t that I can’t evolve and see what (Hollywood’s like today). I’m very clear on what it’s like now and a guy like Ari still exists, so it’s not like it’s not happening.

“At the end of the day, what I always say about Entourage is: Sensitive people can judge it for off color dialogue, but the reality was, these were guys that all really cared about each other and were really loyal. And while they might have said stupid shit, they weren’t against anybody.”

Ellin is aware that Entourage is as popular as ever and wouldn’t envision any drastic changes because of the vocal minority who can’t wait to be offended.

“There’s a whole new generation watching Entourage right now and they’re not watching it going ‘Oh my God what are these people saying.’ That’s a small group of idiots,” said Ellin. “But at the same time, the culture has evolved and there’s things that I understand a lot more than I did then… You grow and you learn, and you learn about other people and different cultures and other ways people live and you grow, it’s just that simple.”

Vincent Chase Channels Present Day Mark Wahlberg

In much the same way that we wonder if Tony Soprano took a bullet between the eyes or Jesse Pinkman had one hit too many, I asked Doug Ellin where he would envision a modern-day Vincent Chase. For those that may have forgot, Chase was the lead Entourage character who always lived with at least one of his three best friends (sometimes all three) and wasn’t in any hurry to settle into a relationship. So where’s Vinny today?

Doug Ellin:

“I really don’t think about it. But I can tell you about when we were doing the show and the movie, which I was reluctant to do. I said, ‘How long can these guys live together.’ And even Mark [Wahlberg] who Entourage was based on, when Mark got married, everyone was thrown out of the house. Which is the normal thing. There isn’t this world where someone gets married, has kids and they live with five guys. I’m sure it exists, but it’s not common. … I don’t know [what Vincent Chase would be doing], but I do know, Mark, who is the inspiration for this show, is living a life right now that I think people would be very interested in watching. He’s got a lot of the same friends (from before he was married), he’s got the same manager he had back then, the same agent he had back then. So, I think there’s still a lot of things as [Entourage] grows that wouldn’t be the same thing as four 20somethings running around Hollywood.

Doug Ellin loosely based “Entourage” on the life of Mark Wahlberg. (Photo by Vince Bucci/Getty Images).

Charlie Sheen Returns To The Screen In ‘Ramble On’

Ellin’s current venture is Ramble On, which is actively being shopped to networks and streaming services. The show has already shot a pilot, which Ellin and producer/friend Ted Foxman funded themselves. Ramble On’s cast seemingly has more star power than the ’98 Yankees. That includes Charlie Sheen, who played a major role in my childhood (thanks mom and dad!) as both Rick Vaughn and Charlie Harper.

For what it’s worth, Vaughn never would’ve slept with Roger Dorn’s wife had he known…

Charlie Harper would’ve, but the man’s a skilled pianist with a full head of hair and beach front property. What did you expect?

Oh, and sorry Mets fans, but you can shove those trumpets up your ass. There’s never been a more electric relief pitcher entrance than that of Wild Thing himself.

While we’re here, let’s give Charlie Harper his flowers. What a life. My man does a few jingles that catch fire and next thing you know he’s rolling out of bed whenever he wants, wearing the finest bowling shirts around and knocking down more 10s than Peter Weber.

Doug Ellin:

“We shot a pilot that I self-financed and produced. It’s Charlie Sheen, Martin Sheen, Kevin Dillon, Kevin Connolly, Jamie-Lynn-Sigler, Harvey Guillén, Kimiko Glenn. We have an unbelievable cast and the show is, in my mind,  it is an evolved Entourage. It is about the culture as it is today.

“This is these guys playing themselves…Charlie, most people know his story, has overcome his past. Drugs and alcohol. He’s trying to get his life and career back on track and that’s what [Ramble On’s] about. Second acts and people trying to figure out what they do for the next 30, 40 years of their lives and I think it’s very relatable to pretty much anybody who’s had early success in life and then tries to figure out what’s next. Like Entourage, at its core, it’s friendship and all of those elements. It’s another chance for me to show the culture as I see it today, which is so vastly different from what it was 10 – 15 years ago.

Sheen, Ellin and some other Entourage/Ramble On cast members will be at Phoenix’s Stand Up Live on April 8 for a live podcast. If I were in the Phoenix area next month, snagging tickets to this show would be priority two, only behind tracking down Thunder Dan Majerle memorabilia.


When in Phoenix, what better to do than seek out Dan Majerle and Charlie Sheen? Copyright 1995 NBAE (Photo by Noren Trotman/NBAE via Getty Images)

And if there’s a third stop on the list, it would entail me getting my eyeballs on new Sun Kevin Durant’s stems. KD’s been walking around on hockey sticks for 30+ years. (Click the tweet, trust me).

Did You Think We Weren’t Going To Talk March Madness?

I’m well aware that we’re in the Ides of March, so you better believe Doug and I talked Sweet 16. March Madness has given us wedgies (figuratively speaking), upsets and shirtless coaches. But I wanted to know who Doug, a Tulane graduate and noted hoops fan, has cutting down the nets.

Doug Ellin:

“I’m going with [Tom] Izzo. I’ve watched Draymond Green and others talk about what a genius this guy is and how he’s affected their lives. I don’t know that I’m picking them to win with money on it, but that’s who I’m rooting for to win right now and I’d just like to see if he could get through [the tournament). I would like to see [Michigan State] win it, so we shall see.

Full disclosure, I know Auburn is out of the tournament, but I was really hoping Doug would say he had been pulling for the Tigers. And that’s for one reason and one reason only: so I could find a spot for the greatest gif in recent college basketball memory. Thank you coach Bruce Pearl. And god bless your dry cleaners (and coke dealer).

All-In On Pickleball

What interests Doug Ellin more than Sparty is pickleball. For those that aren’t familiar, it’s somewhat like tennis and ping-pong and all the cool kids are doing it. The sport’s popularity is at an all-time high and everyone from Pat McAfee to Leonardo DiCaprio is playing. Being that Leo’s hitting the courts, I have to assume some smokeshows outfitted in lululemon are also volleying for serve, but I can’t say for sure.

In any event, as OutKick noted this fall, pickleball has exploded and everyone wants a piece of the game. Kevin Durant recently bought in, as did Ellin.

Personally, my remaining athleticism resides in my thumbs. I’ll text at an Usain Bolt-like speed. And if you so happen to get me on the joystick for an old school NBA Jam arcade battle, be prepared to be read your last rites.

Since those skills don’t seem to pair well with pickleball, I wanted the skinny.

Doug Ellin:

Pickleball is sport anyone can play. It’s social. But you can also take it to the next level which I’m trying to do right now…I got to play with some of the best tennis players in the world last week at the Indian Wells Tennis Center. It’s a community. You know me, at this stage in my life they say you don’t make a lot of friends after your 40 years old. And I’ve met some of my best friends through pickleball. It’s the one thing that I’ve ever had in my life that no matter where I go [I can find a game.]”

Ellin mentioned that he’s played while vacationing in Italy, Florida and other spots.

Everybody’s the same. Everybody who’s gotten into this game has become so addicted and obsessed with it

It’s life affirming but it’s also a really social game and I’ve made tremendous relationships from it. I’m an owner of the Chicago Slice, a Major League Pickleball team. People think I’m crazy, but HBO had a John McEnroe documentary and John McEnroe in 1975 said ‘I’m not playing tennis, it’s not cool’ and quickly after his comments, tennis (at one point) was the fastest growing sport in America. And right now, pickleball is that. Whether you’re competitive or just want great community, it has both elements, which is awesome.”

Michael Strahan Was Made For TV

Entourage had some of the best cameos in any TV series. Tom Brady, Eminem, Mary J. Blige, Matt Damon and more have all had guest spots. LeBron James also appeared in an episode and more than held his own. That’s not all that surprising considering how well he acts on a nightly basis when a defender dares to enter his personal space.

I was curious as to which athlete/musician/celebrity Ellin thought would make the best full-time actor. Ellin, a New York native, wasted little time singling out a former Giant who just so happens to be a Kelly Ripa favorite.

Doug Ellin:

“Brady was great, LeBron was awesome. I don’t know who would be the best actor. Gronk is a natural on camera for sure. Michael Strahan has obviously made it (in television). I told Michael the day he came on Entourage, ‘You’re a star. I would talk about writing a sitcom for you.’ Michael’s obviously a natural, Gronk’s a natural…Tyson was awesome.”

Doug’s the pro here, so I’m not about to second guess him, but I’m going with Iron Mike all day.

Norm! Doug Ellin Is A Cheers fan

It’s obvious that Doug appreciates someone like Norm Peterson who never saw (or tasted) a nightcap he didn’t like. Since Entourage ranks high on my list of most rewatchable shows, I asked Doug to give me a handful of shows off the top of his head that he finds most rewatchable.

Doug Ellin:

I have a different answer each time, but definitely Seinfeld. Definitely Cheers. And Fawlty Towers. I can give you about 30, but those are the three that popped into my head.”

For the record, my five most rewatchable shows follow (in no particular order):


Curb Your Enthusiasm

The Office

King Of Queens (I know my nigthcaps compadre Zach Dean agrees with this)

Eastbound And Down

Honorable Mention: The League

Am I missing one from my list? I doubt it. But if you think these eyes and ears should be fixated on something else, feel free to let me know via email: anthony.farris@outkick.com or Twitter @OhioAF.

Visiting The Jersey (Are You) Sure?

In addition to instantly quotable one-liners, the newest music and episodes full of extras who would seamlessly place within the Maxim Top 100, Entourage was also easily distinguishable by their characters’ unique sense of style.So as is customary for this weekly spot, we point out odd jerseys, preferably in odd places. First, I give you the late, great Sean Taylor (full uniform) running a half marathon alongside NFC East rival DeVonta Smith.

Secondly, in honor of our nigthcaps guest, Mr. Doug Ellin, I give you Turtle from Entourage rocking his finest Bernard (don’t call me Larry) King jersey.

That’s the same #30 that current Knick – and professed Entourage fan – Julius Randle wore while pouring in a career-high 57 points on Monday night inside of The Garden.

What I’m Eating Drinking This Week

Being that there appears to be a pending tequila shortage – because of a lack of agave production – I’m going to drink up as much Avion tequila as I can. I want to ensure I’m filled to the gills should the agave continue to phone it in.

Remember, a failure to plan is planning to fail.

As for Avion, if it’s good enough for Vince, E, Turtle and Johnny Drama, it’s good enough for this middle-aged writer.


Avion tequila is on the drink menu this evening. Photo c/o Entourage/HBO.

Before I end my workday with some Mexican mouthwash, I’ll leave you with a smorgasbord of Entourage laughs. Don’t say I never gave you anything!

Johnny Drama, Pragmatist
by u/HurricaneBetsy in entourage

Alright, there’s nothing else to do here other than to declare…

*OutKick’s Nightcaps is a daily column that runs weekdays around 4pm EST.

Follow along on Twitter: @OhioAF

Written by Anthony Farris

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