• Stay Gold —

    Scott Caan thrives on pushing boundaries on land and sea

    Story — Jason Black
    Images — Hideo Oida

    There’s no denying it. Scott Caan is a charismatic guy. Even now, at 11 a.m. on a Sunday morning, his one day a week off from the daily rigors of shooting the second season of Hawaii Five-O, he’s on. Lounging on the lanai of his two-story, Mediterranean-style white stucco house nestled on the slopes of Diamond Head, he’s chatting about wrapping up the eighth and final season of Entourage, the HBO show about making it big in Hollywood.

    At 35, Caan should know a thing or two about Hollywood. He’s lived around the entertainment industry his whole life. It’s the family business. Acting is in his blood. And, if you’ve seen him in such notable films as the Ocean’s Trilogy and Gone in Sixty Seconds, you know it’s true. He’s good. Real good.

  • But, somehow, he doesn’t seem entirely comfortable claiming himself as a bona fide movie star. He refers to “the arts” sarcastically, not pretentiously. And he’s seemingly more at ease with being seen as a regular guy from the neighborhood that can act then a back lot big shot. Beyond acting, he enjoys a variety of personal interests like surfing, skating, bikes and hip-hop, as well as screen writing and photography, which he discovered later on in life.

    Growing up in LA, he admits to having tough times at home. It was an unconventional upbringing with mom and dad, Sheila Ryan and James Caan. So, at 13, he ended up connecting with some local kids he looked up to and wanted to emulate. “I hung out with kids that I thought were interesting, and they just happened to be hoodlums, B-boys, criminals, skaters and surfers.”

    During his teen years in the late ‘80s and early ‘90s, surfing and skating was on the rise. But it wasn’t cool or commercial yet. In fact, it was mainly for kids from broken homes, derelicts and dropouts who wanted to feel like they belonged. Somewhere. Anywhere.

    “Back then, it was punk to surf and skate,” affirms Caan. “It was its own little culture. Today, six-year-old girls from [Brentwood] get surfboards for their birthdays. It’s not like it used to be.

  • “Now, skateboarding is so blown out. Surfing is so blown out. Hip-hop is so blown out. It’s a whole different thing. When I was a kid, those were the kind of things you did when you wanted to be anti-establishment. It was your way of saying, ‘Fuck you.’ And I definitely fell into that category.”

    At the time, Caan recalls that dad was not amused. “My dad was an athlete, and I always played sports when I was younger. Then, when I started surfing, skating, and dancing, my dad was like, ‘What are you doing? You don’t skateboard, there’s no team. You don’t surf, there’s no team. You guys just hang out on the beach.’”

    But Caan remembers being instantly drawn to it. He felt like he’d found something that suited him. It was his. “I think that it was a combination of being a kid and the people I looked up to, and the people I wanted to be like. I was always an athlete, so I felt like that was the way to go. Also, I wanted to skate and surf, because it was something you did your own way. It was creative self-expression. There are no stats in surfing and skating.”

    Even though he didn’t understand it, Caan is quick to point out that his dad always tried to be supportive of his son’s alternative interests. “My dad, from when I was a kid, was always like, ‘If you’re going to do something, be fucking good at it. Get after it.’”

  • And, over the course of his life, that’s exactly what Caan’s done. In the process, he’s taken risks, pushed his own limits and tackled new challenges. He admits to continually staying busy in order to keep himself sane. He hates being bored.

    “I hate simple, the same shit every day. I can’t imagine how I ended up on a T.V. show. You know? Talk about repetitive.”

    Early on, one thing Caan discovered he had a passion for was rapping alongside Alan Maman (aka The Alchemist). The boys met and hung out even though they went to different schools. Caan was also friends with Maman’s older brother. They all had similar interests in graffiti writing and B-boying. So Caan and Maman got together one day and hatched a plan. “When I met Alan, I was like, ‘Fuck man, let’s try to make a group.’ He said, ‘All right, let’s try it.’”

    So they started writing rhymes together. After a bit, they felt like they had a routine and were ready to cut a demo. Through a mutual friend, Mike Perretta, better known as Evidence from Dilated Peoples, the guys hooked up with a producer willing to help them out, Quincy Jones Jr. Caan and Maman worked tirelessly with him at his studio, ultimately polishing up their demo, and Jones Jr. started shopping it around.

    After a chance meeting, Ice Cube was interested and wanted to sign the guys to his label. “I’m in ninth grade and I’m sitting in Ice Cube’s office, and [NWA’s] first album, Straight Outta Compton, was my bible. I was like, ‘This is the fucking coolest thing ever.’” But Caan also remembers that things didn’t quite go according to plan.

  • The two met with Ice Cube about the possibility of working together. Caan was ecstatic. But Maman wasn’t convinced. “Then I remember Alan said, ‘I don’t like this shit. I’m not a hood. I’m from Beverly Hills. You’re going to put me in a hoodie and have me talk about 40 ounces and shit. That ain’t me.’ I was like, ‘Well, who gives a fuck what we’re doing. Let’s go.’ But Alan talked me out of it.”

    He was like, ‘No, man. Come on, let’s keep it real.’ And I’m like, ‘Fuck, ok, let’s keep it real.’”

    But their luck turned when they coincidentally met B-Real from Cypress Hill. Instantly, the guys hit it off. They had a lot in common and knew a bunch of the same Venice locals. It felt right. And most importantly, B-Real insisted that they maintain their own identity. The Whooliganz, as they were known, were on their way. “Next thing I know, I’m 16 and on tour with Cypress Hill and House of Pain,” says Caan. “It’s still the best time of my life. They were like family. They took care of us.”

    While they were over in Europe as roadies, they were slated to perform their first debut single, “Put Your Handz Up” on a talk show in London called “The Word.” Caan describes it as the English version of David Letterman. But the label wanted them to change up their sound to be less like late-’80s hip-hop and more like early ‘90s house music that was emerging at the time. Instead, the guys ditched the show and went to Amsterdam for the weekend. “On Thursday night, we got on a flight to Amsterdam, and didn’t even tell anybody. We just bounced. Alan, Seth Binzer, the lead singer of Crazy Town and I went and just wild out for four days, flew straight home, and when we got home they were like, ‘You’ve been dropped from your record label.’”

  • That was that. Finished. Finito. From there, Maman opted to plunge behind the scenes and pursue his interest in making beats. He’s gone on to become an accomplished hip-hop producer in his own right, working with the likes of Nas, Fat Joe, Jadakiss, Ghostface Killah and Snoop Dogg. He’s also continued to support old friends producing for Dilated Peoples, Cypress Hill, Everlast (formerly of House of Pain) and even Crazy Town. Currently, he’s signed to Shady Records and working with Eminem as his DJ.

    For his part, Caan had no idea what to do next until he got a call — pure luck — about a movie audition for 1995’s A Boy Called Hate. At the time, he had no desire to give up on his lofty hip-hop dreams. But fate had other ideas, and this part was too intriguing to pass up. The story centers on a kid who gets out of juvenile hall and shoots somebody. He goes on a road trip on his motorcycle with a girl, runs away from the law, and ends up saving her from being raped.

    Caan decided to go for it. “Fuck it, I’m James Dean,” he says.

    He auditioned a couple of times and finally got the part, beating out a teenage Joaquin Phoenix. While on set, he had an epiphany. “When I was on that movie, I didn’t know if I wanted to be an actor, the guy holding a light, if I wanted to push the dolly, if I wanted to shoot or if I wanted to write it. I was just like, ‘This is home. Whatever this is, whoever these people are, this group of misfits, from the grips to the writers.’ They seemed like my kind of people. I knew that this is what I wanted to do for the rest of my life.”

    From the start, he was hooked on the creative process of filmmaking. “I was really into this mix of humans to make one thing. Everybody’s doing something different to make this one thing, and the whole process, I really fell for that big time. I was like, ‘Oh, ok, this is it.’ I still don’t know what the fuck I want to do, but I know I’m in the right world.”

    Immediately upon wrapping the movie, he signed up with Playhouse West, a theatre group in North Hollywood that Caan’s mom had studied at years earlier. He wanted to explore what acting was all about. And he wanted to make sure he learned it the right way. His father’s advice about “getting after it” was ringing in his ears.

    While there, he wrote small scenes for himself and others using a pencil and paper. Finally, on the urging of a friend, he decided to buy a computer and capture a few. Caan and his acting buddies ran some of these homespun scenes by Robert Carnegie, the lead acting coach and mentor of Playhouse West. He liked what he heard and urged Caan to keep going: “Write more.”

  • “So I started writing plays,” says Caan, excited and inspired. “Every Thursday, my mission — there are a bunch of classes at Playhouse West, but Thursday night was the elite class, where you were if you had been there for a couple years, and you hadn’t gotten kicked out, or you hadn’t cried too many times because you were abused, Thursday night was ‘the space.’ It was a lot of good people like Val [Lauren], James Franco, Ashley Judd, Mark Pellegrino, and I. It was a really good group of actors. Every Thursday night, you showed up to battle, and ‘Who’s going to kill it tonight?’ So, my goal was to write something for every Thursday night. I would piece it together, and then we started putting up plays.”

    Sparked by this experience, Caan was hungry to expand their weekend audience from 150 each night with Friday, Saturday and Sunday performances to 150,000. The only way to do that, he reasoned, was to write a movie.

    So he fired up his laptop and got to work. During that period, he banged out a couple of scripts. Some of them sold. Some of them didn’t. But one stood out. It was the script that became 2003’s Dallas 362. It was a movie Caan wrote in only three weeks but he contends was a big turning point for him. It had to be. It was a movie he wrote, starred and even made his directorial debut in. He was in total control from the start.

    “I thought, ‘Fuck, if I’m going to make a movie, and I’m going to be the director, I want to write it in a way that I know it’s not going to drive me crazy, and I’ll be able to do it all.’ So I literally wrote this script in 20 days. I was like, ‘Here it is.’ And the producer, who had seen one of my plays and read a few of my scripts said, ‘Let’s go.’ He had already raised the million dollars to make it. I couldn’t have been more confident in my life, because I wrote it knowing that I was going to have to shoot it. I knew every shot. I was so prepared.”

  • Due to past movie-making experiences, he also knew exactly what kind of director he wanted to be; the kind that knew what they were doing. “I had been in a lot of movies, and I noticed the best directors were the ones that would walk into a room and go, ‘All right. This is what we’re doing.’ Then I saw other directors that would come and bite their nails and go, ‘Ok, what do you think? What should we do here?’ I decided, ‘Those guys suck, and these guys don’t.’ I knew exactly what every frame of this movie was supposed to be.”

    “If someone asked me a question, I was like, ‘This, this, and this.’ The producers were like, ‘Wow, man, you’re going to be a great director.’ I hadn’t even done anything. It doesn’t mean that I’m going to be a good director one day. It just meant that I was on top of my shit.”

    “Still, that movie specifically, there’s a ton of stuff I would have done differently, but I’m super proud of it. I’m super proud of doing everything, and it gave me the confidence to be able to say, ‘Oh, I can totally do this.’ I think that’s a huge thing. I think there are so many people that are talented, but there is part of them that says, ‘You can’t do that.’ The most successful people have a combination of things, and obviously, talent is one of them. But a huge part of it is the confidence to go, ‘Ok, I can do this.’”

    Talent is golden. But confidence is king. In that respect, Caan admires another ‘80s rapper who’s transformed himself into a credible actor, a producer and now, a big time show runner: Mark Wahlberg. They worked together on Entourage. “He’s a good actor. But look at what he’s done. He’s not Lawrence Olivier, but the dude is like, ‘I can do anything. I can produce this. I can make these shows. I can put these people together. Yes, I’m an actor, and I can show up and hold the gun, and everybody’s impressed by me.’ But he’s a smart dude who says, ‘I can do this, this, and this. Don’t dare me that I can’t make a billion dollars next year. I’ll rap. I’ll be an underwear model. I don’t give a shit.’”

    He also has similar praise for another well-known colleague who Caan collaborated with on Ocean’s. “Look at George Clooney, too. He’s a talented dude, but he’s also like, ‘What can’t I do? I’m going to do this. I’m going to do that.’ I guarantee that there are a lot of people out there who can do that as well, but a big thing is being able to say, ‘No. I envision this for myself, and I can really do this, that, and the other.’”

    Caan admires their bravado and seems well on his way to emulating their example with his own string of upcoming projects in the development pipeline. He hints that one is teaming up with his dad.

    His accomplishments on Dallas gave Caan the confidence to branch out and test himself creatively. After the movie wrapped, he discovered that he had a passion for photography. It all came about through working with Phil Parmet, his director of photography. During the movie the two became friends and Parmet taught Caan how to handle a camera.

  • “I’d gotten a camera that year as a gift,” remembers Caan. “He said, ‘I used to shoot with this camera.’ So he taught me about shutter speeds, f-stops, composition, and why he shoots the way he shoots. The preparation for that movie was like school for me. By the time the movie started shooting, in that two-month period, I went from not even wanting to pay attention to cameras, to, ‘Phil, I think, can we be here instead?’ He would smile, and he saw that I’d gotten the bug.”

    Smiling, Caan recalls becoming totally obsessed with clicking away and capturing the moment. “I was shooting and shooting. I was taking more pictures than anything else. I wanted to travel to shoot photos. Someone said, ‘Let’s have a birthday party for you this year.’ I’m like, ‘All right, well, I’m going to show some of these photos that I shot.’”

    And that’s exactly what he did. In 2004, he did a one-man show for his birthday at his friend’s menswear store called Kingsbury in LA. For his debut, he only showed ten prints. But a few of them sold and that inspired him to keep shooting. Next year, he returned with 20 prints. He did it for five years in a row. Shoot. Print. Show. Repeat. His goal, every year, was to come up with a bigger and better show of new photographs. Finally, in 2009, he collected his best images together in a coffee table book called Scott Caan Photographs Vol. 1.

    “The last party I had was the book opening on my birthday,” he says proudly. “I haven’t really shot any photos in about a year and a half, but it’s because I’m on this show.”

    The secret to his obsession with photography lies in its purity and its permanence. “To me, photography is one of my favorite things because I don’t give a shit about what it’s supposed to look like. When you write something, 30 people are going to give you their opinions, and then you have to rewrite it. You direct something and everybody has an opinion. You produce something, it’s even worse. As an actor, you have a director telling you how to do it. Me, and that thing [the camera], we’re just out there doing it. If I see a photo, and I like the way it looks, I’m going to print it.

  • “Then, of course, someone goes, ‘Oh, I like this one. I don’t like this one.’ But they don’t change. You can’t change a photo. It’s like, ‘That’s what I took. If you don’t like it, I’m sorry.’”

    Then the conversation swerves toward motorcycles, a love affair Caan’s had since his rebellious teenage years riding dirt bikes. And let’s face it. Who doesn’t love to look cool like James Dean or Paul Newman blazing down the highway? “If I really loved bikes, then I should get a Ducati and do 120 around turns. But I like doing a burnout with a suicide shift and doing beelines through traffic because it makes me feel like I’m Dallas from The Outsiders. Those are just the kind of people I looked up to.”

    At the moment, Caan’s cherished 1960 Panhead, a bike he’s had for six years, is in the shop. Another buddy from high school, Yaniv Evan from Powerplant Choppers, is working on it and fixing his brakes.

    Chuckling, Caan launches into the ongoing repair saga that is this bike. “I called him up, ‘Yaniv, this back brake doesn’t work.’ The front brake is irrelevant. It’s a suicide shift with a back brake that’s not working. ‘It’s a death trap.’

    “He said, ‘Well, what do you mean they don’t work?’ I’m like, ‘Dude, I’m telling you, the rear brake does not work.’ He said, ‘All right.’ So, I drive the bike over to him.

    Then I get a phone call that night at 1 a.m. ‘What’s up, dude?’ He said, ‘I’m in the hospital.’ ‘What happened?’ I said. ‘I crashed your bike. The fucking brakes don’t work.’

    "But he wasn’t kidding,” Caan says, pausing for comedic effect. “It was as if he was giving me new information that I didn’t know about.”

    Like his passion for vintage bikes, Caan also has the same fascination with surfing. He enjoys riding all kinds of exotic, one-of-a-kind boards. Sometimes, it’s just to get a reaction in the water. “I ride Alaia, and weird boards all the time. I love the feeling, but I also love people going, ‘Holy shit. He’s riding a piece of wood.’ There’s something about the show-off side of surfing and skating. It’s not as fun if someone didn’t see you do it.”

    Later, we round up the troops, including his girlfriend, grab some surfboards from his storage unit in the garage, and walk a few blocks down to the beach. On the way to Tongs, a local surf break, a car driving by slows to a crawl, obviously recognizing the actor. A camera pops out on the driver’s side and starts taking photos while the passenger yells out, “We love you, man.”

  • “Thanks,” says Caan, turning around. He graciously stops on the sidewalk and poses for a few candid shots with his Alaia, a traditional Hawaiian wooden surfboard in one hand and a casual shaka in the other. He’s polite, giving them a story and a memory to share with friends and neighbors. After a minute or so, he walks on.

    “You’re one of us,” gushes the guy from the car, encouraged by Caan’s graciousness. He’s referring to the fact that because of the show, locals here on the islands have claimed Caan as one of their own. He’s now a member of the ohana in the same way original Five-0 actors Jack Lord and James MacArthur were before him.

    “God bless,” Caan calls back as the car speeds off. He hangs a left down the public access alleyway towards the surf. At the end, he jumps into the water and paddles out toward the outer reef break and the clear blue horizon.

    Check out Part II of our Scott Caan feature here...

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