Welcome to Random Roles, wherein we talk to actors about the characters who defined their careers. The catch: They don’t know beforehand what roles we’ll ask them to talk about.
The actor: Over the last 25 years, Scott Caan has developed a reputation for playing strong-minded, wise-cracking characters. After beginning his career in the early ’90s as one-half of the hip-hop duo the Whooliganz, Caan made his professional acting debut in the indie A Boy Called Hate, a crime drama in which his father, James, played a small role.
From there, Caan enrolled at Playhouse West in Los Angeles to study acting and broke out at the turn of the millennium in several studio films, including Enemy Of The State, Varsity Blues, Ready To Rumble, and Gone In 60 Seconds. But the actor is perhaps best known from this period for playing one of the Malloy twins in the heist film Ocean’s Eleven and its two sequels, where he starred opposite George Clooney, Brad Pitt, and Matt Damon.
Along the way, Caan has starred in, written, and directed his own plays and features (Dallas 362, The Dog Problem, Mercy). But in recent years, he’s found a home on television. After appearing in the final two seasons of HBO’s Entourage, Caan starred for 10 seasons as Danny “Danno” Williams in CBS’ Hawaii Five-O, a role that earned him a Golden Globe nomination for Best Supporting Actor in 2011.
Nearly three years after the end of that show, Caan has returned to the procedural genre in Alert: Missing Persons Unit, a Fox drama that premiered earlier this month and airs on Mondays. Set in the Philadelphia Police Department, the series follows exes Jason Grant (Caan) and Nikki Batista (Dania Ramirez), who search for the loved ones of others—all while trying to uncover the truth about their own son, who disappeared from their lives six years ago.
On a recent January afternoon in New York City, Caan sat down with The A.V. Club to discuss new acting challenges, the elusive nature of chemistry, working with his late father, living and partying with Paul Walker, clicking immediately with his co-stars in the Ocean’s franchise, and more.
Alert: Missing Persons Unit (2023)—“Jason Grant”
The A.V. Club: Jason and Nikki seem to see the world and approach things differently, but they complement each other. There are clearly some unresolved feelings between them, and there is this push-and-pull between the past and the present. How are you and Dania choosing to play that relationship, where your characters have that history as exes and co-parents of another daughter but now are romantically linked to different people?
Scott Caan: I think we try to avoid that television cliché of “Will they get back together?” But for me, it is an interesting thing because when you really love somebody, you deal with them a little differently than you do somebody that you’re just working with. So [as Jason] my instinct might be to snap at her, my instinct might be to tell her she doesn’t know what she’s talking about, or vice versa. But because of what we share together, it adjusts how you act in those scenes, and that’s not preconceived.
I remember we were shooting the first scene [of the pilot], and it was in a car and kind of written like an argument. My instinct was to just go at her and argue how I would normally argue, and the director came in, and he’s like, “Hey man, there’s a lot of love here. It’s not necessarily that [antagonistic].” That really adjusted the way I thought about it, and that sort of set the tone for how we deal with each other.
I love Dania today because we’ve been working together for four months, and we’ve been through a lot of stuff together. But on that day one, I didn’t have that kind of [loving] feeling for her. So I had to have a director come in and be like, “Hey, don’t forget about that.” I was like, “Oh, that’s a great note,” and it adjusted the way that the rest of the episodes played out for us relationship-wise.
AVC: There is a time jump from the day Nikki and Jason’s son, Keith, went missing to the day they sign their divorce papers in the pilot. What kinds of early conversations did you have with the executive producers about fleshing out these characters and understanding what they went through over the last six years?
SC: That’s a good question, man. Honestly, not a ton. I was really just doing my own homework and figuring out how I’m going to approach it. I feel like, as actors, we want to work and dig in and put backstory together and figure out who we are, and it all kind of just goes away when you get on set. I don’t want to just show up and not be prepared. I don’t want to just memorize my lines and hit my mark. I want to have ammunition. But I find time and time again, the work really happens between the two people, right? I won’t stop working that way, and it’s not a waste of time, it fills up space. But the last thing you want to be doing when you’re acting in a scene is thinking about the past or thinking about what your idea of the scene is.
My favorite acting or my favorite actors always are the ones that are the most in the moment, and it’s really about chemistry. It’s really about what’s happening right now. Especially on a procedural show or any kind of show, the history and the character development happens between the actors as you move forward throughout the series, and that’s where it grows, really. A writer can write all the shit that he wants—and I say that as a writer too, I’m not disrespecting that part of it—but we’re the ones who make it happen when the camera’s rolling and all that stuff. You’re better off just taking your co-star out to dinner every night before you start working, because whatever you create, whatever you come up with, whatever’s naturally there, that’s gonna show up on screen—and that’s the good stuff.
AVC: You mentioned during a press conference last month that there are “a lot of acting problems” in Alert that you enjoy and that have made you feel uncomfortable. How has playing Jason in the last four months alone already pushed you as an actor?
SC: I think it’s a combination of the writing and Dania personally. She pushes buttons in me that haven’t been pushed before, and there’s no preparing for that. We’re constantly trying to, as actors, make the thing as real as it can possibly be. And in these horrible situations, if you actually approach it properly, it’s traumatic, and it kind of fucks you up a little bit. It’s horrible to go to work every day.
AVC: You’re essentially reliving every parent’s worst nightmare every day you go to work.
SC: I don’t know why this comes to mind, but did you ever see that movie Natalie Portman did where she played Jackie Kennedy [Jackie]? And by the way, I’ve never talked about Natalie Portman. I don’t know why this just came to mind, but it did. [Laughs] I was watching that going, “Man, she must have wanted to kill herself at the end of that movie because she’s a good actor, and she’s not showing up faking any of that. She spent four months making that movie, reliving the moment that her husband was shot in the head.” And it’s not that we’re doing something as heavy as that. But in a way, Dania is a serious actor. I try to pretend to be a serious actor. We’re showing up really trying to go through these moments and have these experiences. And it’s a drag, but in a good way.
Those are acting problems that I haven’t necessarily had to deal with before, and it’s challenging and new for me, and it makes me not feel like I’m an expert at something. Young actors will always ask, “What do you do? How do you do this? How do you do that?” My answer is usually: “I have no idea, man. I’m figuring it out as I go along.” If we get to a point where we’ve got it figured out, then we might as well try something else or quit or move on to a different profession.
The reason acting is interesting to me is because I am constantly learning new things and figuring out how to do it. I’ve been doing it for 25 years, and I feel like I’m just getting started in a sense, which is healthy and good, and this show specifically has really challenged me in a way that makes me go: “Shit, I don’t know what I’m doing.” I’m just trying new things. I’m trying to figure out how to be constantly emotionally available in these situations. It’s heavy and not yet mastered, and it’s something I’m still trying to figure out how to do.
Hawaii Five-0 (2010-2020)—“Detective Danny ‘Danno’ Williams”
AVC: For a lot of actors, especially after playing a character for a long time, there are certain mannerisms or parts of past characters that might creep into the new characters they play. Do you see any similarities between Jason and maybe Danno from Hawaii Five-O or any of the other characters you’ve played?
SC: I’d like to say no, but I guess the answer is of course, right? I don’t care if you’re playing a part that’s the opposite of you. You gotta figure out a way to put the most of you into that person that’s not like you, so yes, I guess the pitfall of doing the same character for such a long time is that you can’t help but have little bits or mannerisms from other characters come into play. When you do a movie, you can really dig in and become somebody else for two months for 90 minutes of cinema, as opposed to when you’re doing a show, [and] the character kind of becomes you or whatever version of yourself that you’ve created from the beginning. After two seasons, three seasons, there is no separation between you and [the character], which is good and bad, right?
AVC: Ending a show almost feels as difficult as starting and launching one. How do you feel about the way Hawaii Five-O wrapped up?
SC: To be honest, I don’t remember how they were wrapped up. [Laughs] I literally have no clue. You could tell me, and I’d be like, “Okay, yeah.” But as far as a job, man, the people I was working with on a daily basis, even the ones I didn’t like, were still family. I was closer to a lot of the people on that show—crew members and other actors—than I was with family members.
Alex [O’Loughlin] and I went through so many ups and downs. That dude’s my brother for the rest of my life. And sometimes I wanted to strangle him, and sometimes he wanted to strangle me. [Laughs] But that dude’s my family until the day I die.
AVC: You and Alex became the show’s fan-favorite duo with your explosive ability to banter and bounce off of each other on and off the set. What do you miss most about working with him in particular?
SC: Look, I think that’s the key to any show: The people you’re watching have that banter. And by the way, let me just reiterate: I didn’t want to strangle him more than I did want to strangle him. But I’m just saying after 10 years, there were moments he wanted to kill me [Laughs].
I just miss working with somebody [where] we have so much history and it was just easy. You couldn’t throw us an acting problem that we couldn’t solve together. And I don’t mean any disrespect, but when you’re trying to write 25 episodes in nine months, some of it is not going to work on the page. And a lot of the time, they would hand us something [where] Alex and I had to figure out how to make it work. And by the end, we didn’t really have to talk. I’d just look at him, point to a line, and he’d be like, “Yeah, yeah, I got it.” We’d know how to get through scenes, and then I knew his strengths. When there was something that could be fixed with his strengths, I’d back up. And when he knew that there was something that I could fix, he would back up. It takes a while to build that.
There’s a power struggle in the beginning of a show. I think I’m really good at certain things, but the people I’m working with don’t know that I’m good at it. I feel like I know how to make a scene that’s not working work, and when you’re working with new people, they may think, “Well, why does he think he knows?” And it’ll take me six or seven episodes for them to go, “Oh, okay, Scott knows how to do that part.” And then there’s certain things where I have to figure out, “Oh, Dania knows how to do that part.” We’re just getting there now, and who knows if we get another season, right? So we might just have to start over with another show or we’ll continue on.
The thing with Alex and I is, we could figure anything out easily and our egos would, for the most part, go this way [motions his hands separating and going in different directions]. We’re two alpha males. Season one, we were like, “I know!” [Motions his fists to clash] “No, I know, I know! I got this.” By season four, five, and six, our egos kind of floated away a little bit, and we were able to work together and figure out anything.
Ocean’s Eleven (2001), Ocean’s Twelve (2004), Ocean’s Thirteen (2007)—“Turk Malloy”
AVC: What do you remember from auditioning for Turk and then being paired up with Casey Affleck to play your twin?
SC: Man, I remember being really into Steven Soderbergh’s early independent movies. I think I had seen Out Of Sight. Owen and Luke Wilson were originally supposed to be Turk and Virgil, and they ended up passing for some reason, and it was just very quick. I got a phone call: “Hey, will you come audition for Steven Soderbergh?” And I was already like, “Oh man, that guy’s the man.” I didn’t know, really, who was in the movie, [but] I think I knew that it was Brad [Pitt] and George [Clooney]. I went in, I auditioned, and literally maybe later that day or the next day, they said, “Hey, you got this part.” And I went to the table reading two or three weeks later, and I walked in, and it’s Brad and Matt Damon and Don Cheadle and Bernie Mac. That’s where I met Casey, and we did the reading.
Casey and I didn’t even really talk that day, and two weeks after that, we were on set shooting the scene where I’m driving the truck and he’s driving the remote control [truck]. That was basically when we met. And the great part about that was, I said to Steven, “Hey, can I play a little bit?” And he said, “Yeah, yeah, you can improvise or just mess around.” And whatever Casey’s improvisational style is, mine was the exact same way, and we just clicked, man.
By Ocean’s Thirteen, I think they’d write in the scene, like, “Scott and Casey argue.” [Laughs] I think they didn’t even write all the dialogue. They’d be like, “Let those two do it.” I just got such a kick out of him, and I think he got a kick out of me too, and that goes back to the chemistry. I could have planned all this shit that I felt about Casey before going into that movie. But the second I met him, I was like, “Oh, this dude, he makes me laugh. And I like busting his balls.”
AVC: You don’t get those kinds of A-list actors working together on a single project like that anymore. Do you have any particularly fond memories from shooting those movies?
SC: Yeah, there are a lot of answers to that question. But I was positive that, working with all these gigantic movie stars, someone was going to be a jerk, and it was the opposite. Not only are they the most talented dudes, [but] they’re also the nicest and coolest people to be around. So the whole experience of doing all three of those movies, it was just fun from beginning to end. We never wanted it to end. Most movies, you’re, like, counting down the days. Those movies, we were like, “Can we extend a week? Can we shoot an extra couple of weeks?”
Steven Soderbergh is, without question, to me, one of the greatest directors of our generation and the coolest person to work with. There’d be a 10-page scene with Brad, George, Cheadle, Bernie Mac, all of us, and we’re thinking, “Okay, this is going to be a 15-hour day.” And we show up, and Steven shoots one shot, and he goes, “All right, everybody, go home.” It’s like a dream! [Laughs.]
You’re working with a dream director, a dream cast, a dream producer, the great Jerry Weintraub—there was no one like him, nor will there ever be anyone like him. I mean, I felt like a movie star, man! [Laughs] I was treated like a movie star. I don’t think anything will ever be like that ever again, and to think that it’ll be like that again, I know I’m just going to be let down. I think it was such a rare, amazing experience.
Entourage (2009-2011)—“Scott Lavin”
AVC: This was your first time playing a character on television across a longer period of time, and you shared a significant amount of screen time with Kevin Connolly. What did you learn from watching him that you’ve wanted to emulate?
SC: Well, a couple of things, man. I did a movie—one of my first movies—in the late ’90s [where] Kevin Connolly came and did a small part. I just remember watching him thinking, “Man, who is this dude?” I didn’t know who he was. I know Kevin’s been working since he was a kid, but I just remember doing this scene with him, thinking that there’s something special about this dude. He’s just so comfortable on camera, and he’s just funny and charismatic. So it really stuck in my head, and then the first scene I did on Entourage was with him, and it was like I was immediately right back to 1999.
Working on that show was my first time ever doing television. I remember when Entourage first was being shot. They were doing the pilot, and I think they asked me to come test for one of the parts, and I was like, “I’m not doing television!” And then cut to eight years later, and I’m begging [creator] Doug Ellin to keep writing me onto the show. But that was my first experience doing TV, and I loved it. It was amazing. They called me about doing Hawaii Five-0, and I thought, “Hey, I’m sure it’ll be just like this.” And it was not anything like on Entourage.
But I got spoiled with Entourage—it was almost like the television version of doing Ocean’s Eleven. Everybody was having a good time, laughing and eating good food. And basically, coming to work was like a party. Maybe it’s because I’ve been doing dramatic TV, but when this is all over, I want to try to get back to a show where all we do is have fun because I’m sick of being upset [laughs].
AVC: We need you in a rom-com. Everyone is trying to revive the rom-com these days.
SC: Hey, man, that’s my jam! I’ve written a bunch of romantic comedies that have never been made.
A Boy Called Hate (1995)—“Steve/Hate”
AVC: Let’s go back to the start of your career, when you played opposite your father, James, in your professional acting debut. How did you go about making the transition from rapping to acting in the mid-’90s?
SC: I was in music, and I was not interested in acting. This director [Mitch Marcus] came to a show that we were playing. We were doing a show with Cypress Hill and House Of Pain and Funkdoobiest back in ’94, I think it was. And he said, “Hey, man, will you come audition for this movie part?” And I didn’t really take it seriously. I went and got the part, and the role for my father was just a one-day part. And the director, once I got the part, was like, “Hey, would you see if your old man would do this?” So I called my dad. He’s like, “Yeah, I’ll come and do it.” So I wouldn’t say we were [acting] opposite each other; he just did a quick little day or two on it.
But man, I had no intention of being an actor. I thought acting was kind of silly, and my dad always downplayed it and made it seem like it was a silly profession. But when I got on that set, it changed my whole world. I didn’t know what I wanted to do; I didn’t know if I wanted to act, direct, carry the lights, bring the food. But whoever these groups of strange people were, I knew I was a part of these people. I was like, “Oh, I found my people.” And then after that, I wanted to take it seriously, so I went and studied at Playhouse West, and that’s where I got into theater, writing, and directing. And that was like my home—[and it] still is. But that’s where I really got into writing plays and trying to direct my first movie.
AVC: In addition to working on both sides of the camera, you’ve also written, staged, and starred in some of your own plays. Will you still be doing more of that in the future?
SC: Yeah, I’m always writing. I can’t help but write. I always say acting is what I do for a job and writing is what I do because I can’t not [do it]. I started writing plays because I couldn’t get the rights to the plays that we wanted to do, and I was writing plays during Hawaii Five-0 because that’s all I had time to do in my off-season. It was a short, little six-week run, and I wrote plays as [a kind of] therapy. If I was stuck on Hawaii Five-0, I would write things to give myself an opportunity to do something different than what I was doing.
Mercy (2009)—“Johnny Ryan,” writer and producer
AVC: How did working with your father on A Boy Called Hate compare to working with him almost 15 years later on Mercy?
SC: The difference was, he was doing me a favor. He came in, and I wasn’t intimidated by him, as most people would be working with James Caan. That would really scare the shit out of most young actors. I was 18 years old. But I was just talking shit with my dad. We were having conversations that were similar to conversations that I had had.
And it’s funny—I never really thought about it until you just asked me this question, but it really brought to my attention that good acting is two people paying attention to each other and bringing the most of their off-screen life onto the screen. I never want to get “caught” acting. I never want someone to watch me be an actor. The biggest compliment to me is if we’re having this conversation and someone says “rolling” and they don’t see a difference. A lot of actors, they’ll be talking to you like this, and then you hear “action,” and then they’re like, “Okay.” [Switches from happy and playful to very serious] And now they start acting.
So working with my father really, I think, subconsciously showed me, “Oh, man, he’s just being himself.” [There are] variations of his own personality, but that’s what makes somebody good. You’re watching them be them or whatever version of the character they’ve created, and then the difference later on when we were doing Mercy is I was the boss. [Laughs] I had to tell him, “No, no, no. I don’t like that take. Let’s try that again.”
Varsity Blues (1999)—“Charlie Tweeder”
Enemy Of The State (1998)—“Jones”
Into The Blue (2005)—“Bryce Dunn”
AVC: You starred opposite James Van Der Beek and Paul Walker in Varsity Blues, which in many ways felt like a classic coming-of-age story set against the backdrop of this societal obsession and fascination with football. What did you enjoy most about playing this cocky, hard-partying wide receiver, and what do you remember most from working with James and Paul? [Editor’s note: Caan and Walker also co-starred in Into The Blue.]
SC: That was the first big role I had in a studio movie. I had just done Enemy Of the State, where I just kind of chased around Will Smith for four months. I didn’t really have a lot to do as an actor. I was just kind of there, and I had done a bunch of independent movies at the time.
But I got that part. And look, man, I dropped out of high school. I didn’t make it to college. The way [director] Brian Robbins had that movie set up was he had us all go to these tryouts, where they had all the football players in Texas that didn’t actually go on to play pro ball, and those are the guys that were all the football players [in the movie]. He also structured it in a way that we shot all of the dialogue scenes and all the action scenes, minus the football, first. Then the last 40 days of that shoot, we were just on a football field doing all of the football stuff.
So by that time, all of these guys, these athletes, were basically living in our apartment. Me and Paul Walker met right away, and we decided we were friends. [Laughs] We got an apartment together, and half of the football team was living on our couches. We were dating all the cheerleaders that were playing the cheerleaders. It was literally like going to college [and] playing football without the school part. I thought, “If this is making movies, I’ve got the greatest job on the planet.”
You talk about digging into a character and figuring out who you are. We were those dudes that whole time. I was going out every night, wilding out, acting crazy, chasing girls, drinking—[but] not really drinking. And oddly enough, James Van Der Beek kind of was like the oddball. We didn’t really kick it with him too much. I love the dude, but he was kind of like the outsider on the movie. I think a great director does things like that, whether consciously or subconsciously. But Brian Robbins set it up in a way that everything you see on screen, we were actually doing [in real life], and that’s how we were living. It was crazy.
One Day As A Lion (expected 2023)—“Jackie Powers,” writer and executive producer
AVC: You recently wrapped production on a film called One Day As A Lion. The synopsis alone sounds like a whirlwind. You play a down-on-his-luck father attempting to save his son from juvenile delinquency. But after failing to collect for a mob, your character finds himself on the run with a waitress-turned-hostage, with whom he forges an unlikely alliance. Deadline reported that it’s inspired by your personal life, so that begs the question: How is it inspired by your life?
SC: Inspired in the sense that all of the characters are based on people that I know and that I’ve grown up around. I have a weird upbringing. My mother [Sheila Marie Ryan]’s side of the family are all stuntmen, so they’re like cowboys. And then my dad’s side of the family are all obviously like these New York wise-guy types of dudes. So I grew up between cowboys and wise guys. [Laughs] So all of the characters in One Day As A Lion are like these cowboy folks and these wise guy folks kind of clashing, and my character being in the middle of all of this.
I had an experience when I was younger in juvenile hall that I wrote into this movie, [which is] about this kid who ends up in juvenile hall. I wasn’t a “good” kid, but I didn’t deserve to be in juvenile hall [for] what I did. So it’s a story about a kid trying to get past and move through his childhood and upbringing because he could have, by all rights, ended up in a really shitty situation. It’s about my character in the movie taking my son out of this life that I’ve set up for him and doing my best to save him, and it’s in the midst of all these insane people.
So it’s from real life in the sense that all the characters are people that I grew up around, but the real core story is about a father trying to right his wrongs by saving his son from the life that he lived himself. And it’s also trying to be funny. It’s me writing a part for myself where I’m not this stoic, tough guy, because I feel like that’s the rule [for me as an actor]. Like, “Oh, yeah, you’re going to play a cop [again].” On the inside, I feel like Woody Allen. [Laughs] I’m a neurotic, crazy dude. I present as this tough, stoic dude, but I’m really just a fucking mess.
AVC: Looking ahead, do you have a dream project that you’d like to pursue or a role that you’d still like to play one day?
SC: Look, man, the TV game has turned into something that it never was. I originally wanted to just be a filmmaker; I wanted to make movies. And now I really would love to try to create and run my own show because I feel like that’s a possibility now. But all I hope is that I can continue to be creative and things will change in this business again, and maybe we’ll get back to movies, and maybe I’ll be writing movies. But specifically, a dream part, no. But to be able to write something that I’m in or write something that I direct [like Dallas 362 and The Dog Problem], that’s always what I’ve been after since I was 18 years old. So in what platform or with which characters, I can’t say specifically. But hopefully, [I’ll] write, act, direct, produce, or just stay involved. I don’t ever want to get to a point where I don’t want to keep playing.