Alex Wolff was 6-years-old when he starred alongside his older brother Nat Wolff in "The Naked Brothers Band," a family project that was later used as a pilot for the hit Nickelodeon show of the same name. Filmed by their mother, actress and writer Polly Draper, on location in their New York City home, the mockumentary-style film followed the young brothers through the trials and tribulations of starting a band. Alex and Nat, then 9, wrote most of the music in the film, which was produced by their father, jazz pianist Michael Wolff.
For Alex, the youngest son of two eccentric artists, it was never a question of what he wanted to be when he grew up. Despite their mother's early reservations, Alex and his brother, now a bonafide teen heartthrob thanks to his work with John Green, both pursued a career in acting. It was a question of which kind of multi-hyphenate he wanted to be.
"I think sometimes the problem with young kids doing this kind of stuff is that they think, at like eight or nine years old, 'I'm gonna be an actor and I'm gonna win an Oscar.' But I think Nat and I were like, 'We're gonna mess with the crew members and have a lot of fun,'" Alex told MTV News. "It made it really easy to act, and I got this intro into acting that was like, you're having fun with your friends and it feels natural, even in front of a bunch of cameras. I didn't really think about the grand trajectory of it all. I was just having fun with Nat."
The 18-year-old actor-musician-writer-director wunderkind credits his New York City upbringing with his unique look at stardom.
"I like LA, I really do, but I'm really a New Yorker," he said. "In New York, there's a feeling that you're not praised or treated too preciously. No one ever feels too important because someone on the subway will reassure you that you're not."
"It's so interesting and weird," Wolff added. "I don't know anything else. That's why there's a very select group of movies about young people that I really connect with, and the movies in New York -- like 'Mean Streets' or 'Midnight Cowboy' or 'Taxi Driver' -- it's like yes, they get it. I really love it. I'm obsessed with New York. I want to marry it, maybe bear a few children with 42nd Street."
New York City is also the source of his inspiration. Alex recently wrote, directed and starred in his own short film "Boots." Shot in the streets of Jay Z's concrete jungle, "Boots" isn't his first short -- Alex has been making shorts since he was 14 -- but it's arguably his most personal. Inspired by a former flame, the 16-minute tale tells the story of Noah (played by Alex), an emotional teen who loses the girl of his dreams and spends the night lamenting in his grief. But a chance encounter at a 24-hour diner ultimately changes his perspective on things. (You can watch "Boots," exclusively on MTV, below.)
"Boots" was originally written on the recommendation of some of his producers for a feature film he was working on at the time. It was a way for Wolff to further develop a character that he felt deeply connected to.
"I had written this feature based on a short story I had written one night when I was really angry," Wolff recalled. "So I thought, 'What if I just kept that feeling?' It became this dark comedy. Noah is angry and aggressive but he's also sensitive and kind of funny, kind of like myself."
"This was 10th grade for me, when everything felt so urgent, and I was so sensitive," he added. "Even if you don’t want to admit it, I think when you’re in 10th grade, you’re never more sensitive in your life. You're just so vulnerable and so angry, or at least I was. I think I was a messed up 10th grader. I had all of these feelings, and if I had a really rough night, it felt like the end of the world."
After fronting around $8,000 of his own money for the project -- with another $425 from his brother Nat because "he paid for all of the food" -- Alex, running on "four or five hours" of sleep a night, filmed the short over several days in New York City. He employed a method he learned from his mother all those years ago during his "Naked Brothers Band" days: the sneak and run.
"It was insane, but I knew it so well, and I know New York so well," Wolff said. "I knew which streets I wanted to shoot on. I was like, 'Alright, there aren't any cops in Tribeca, over in this area, so let's steal this shot while we can.' And there's one part where I have to scream, and I'm kicking s--t in the street, and I knew exactly where we had to shoot that because there's one, long block that never has any police. There were people shouting from their windows, 'Shut up!' And I had to yell, 'One more take! One more take!' It was so New York. It was great."
After a passionate night of cursing and screaming around Manhattan, Noah's journey through the city ultimately brings him to a diner, where he ultimately finds his salvation in a stack of fluffy french toast, a much-needed nap and a cheery group of outsiders who help him understand what it truly means to be young.
"It's so funny because I'm so hypocritical," he said. "The whole short is about how being 16 and drunk at a diner in love with a girl is so small compared to this old married couple who have been together for 30 years. But I still have those moments where I get so wrapped up in my own mind, in my own darkness, that I can't imagine life any other way. Being young, and it sounds so pretentious, but it's a state of mind."
"I have a lot of energy and passion, and a lot of times I don't know where to put it, which is why the short was so good for me," he added. "I put a lot of passion in it. Sometimes, I'll just get obsessed with one things -- so obsessed -- and it's dumb. I'm kind of like an open wound all the time, and that's hard. It's hard to deal with, especially in this industry. Every time I leave a movie, I feel like I'm going to die. Because you connect with these people and then they all leave. I wish I wasn't like that, but I am. I think everyone is a little bit troubled, which is why the art is so important to me."
It's those kinds of moments -- the darker, more internal ones where the wound feels most exposed -- that differentiate Alex from his brother Nat the most. The brothers have been making music together, professionally, for the better part of 10 years, but it hasn't always been a smooth transition. Nat has described his middle school years as "absolutely miserable," saying that he "self-alienated" himself among his peers.
"Nat, in general as a person, is more aware of what's going on around him," Wolff said. "We go places together all the time, and you can kind of see from the short, I'm like energy moving in all different directions, and Nat helps me color inside the lines a little more. So I think he felt alienated because he saw that kids were being mean. I just had so much energy that I didn't really care until it would be blatant and kids wouldn't invite me places. That's when I started to figure it out."
"It was almost more painful because I didn't see what was going on," he added. "I was just really excited. I really didn't understand why people didn't like me. I didn't get it. I felt that way until junior year of high school. 'Why don't people just like that I'm excited about this stuff?'"
In his junior year, Wolff transferred to school for young artists working in film or on the professional stage. (Although, it was Hank Green who helped Wolff ace his chemistry course. "I was doing chemistry, and it was way too hard, so I watched all of his videos and I got an A, so thank you, Hank," he said, smiling.)
"I met a lot of kids who were artists, and dancers, and they were really passionate too," he said. "So I was like, 'Cool! We can talk about this stuff and no one wants to kill each other.' We could be happy for each other, and that was really great for me because I had a really rough time with people not liking that I was doing other stuff than what they were doing."
Still, Wolff can't image going through something as life-changing as childhood stardom without his brother.
"We really did bond over that, and we still bond over it," he said. "It's one of those things that we do talk about a lot, like, 'Man, that place really sucked. Those kids were really not nice to us.' But now people are nice to us, so f--k those guys."
"Boots" is currently making its way around the film festival circuit, and next year, Wolff will appear in the much-anticipated "My Big Fat Greek Wedding 2" and the romantic comedy "The Standoff." He and his brother are also gearing up to work on new music for their band, aptly called the Nat & Alex Wolff Band. For now, Wolff says he doesn't mind being "Nat Wolff's little brother."
"I love to be in the same company as Nat," he said. "He's awesome. He's great at everything he does. But we get sick of each other all the time. We're with each other so much. Now that we've been filming movies, it's more separate, but I don't like being that separate. It's better when we spend a lot of time together and we get sick of each other -- I like that better -- than when we come back after a few weeks apart and it's kinda weird."
"But I've been doing so much," he said. "I filmed four movies this year, and I'm just about to start shooting another one. And we're so different as people. We kind of look alike, but I'm such a different person that I think that connection in people's brains will naturally fade away. But I don't really, I don't mind. I just want people to see my movies and develop their own opinions."
However, he does admit that maybe things would be different if he wasn't doing the things that he loves... like writing, directing, acting, making music, performing, falling asleep at diners, etc.
"I'm sure if I was doing nothing, I'd feel really sh-tty," said Wolff. "But I'm doing all this cool stuff, I just feel like we're doing different things. If we were both in John Green movies, it would probably be harder. If I was Isaac and Nat was Augustus, there probably would be a little bit of sibling rivalry -- but there isn't."