Even before Andy Fickman met with Amanda Bynes at a Starbucks in Los Angeles to see if they would connect, the director was already fan of her work on All That and The Amanda Show, which his son, Austin, watched growing up.
"One of my first jobs was doing development for Gene Wilder, and so there was a lot of that type of comedy, a lot of Gilda Radner that I always remember seeing in Amanda at such a young age, thinking you don't teach someone that," Fickman said.
But, he said he walked away from his first meeting with the Nickelodeon star "blown away by how smart and creative she was and the notion of how to get into this very, very difficult dual role."
"The brilliance of Amanda was her ability to put the comedic spin and add something on there," Fickman gushed of his lead. "So there would be a line there, but she would take it and add an extra Amanda-ism to it that made it even funnier.
And Bynes was so hilarious while filming that Fickman said they often had to do multiple takes of a scene "because the crew and the cast could not handle it."
Fickman remembered Jared Padalecki "being so great" when he auditioned for a role, but he had just filmed the pilot for Supernatural, "So our schedules weren't going to work. But he was wonderful and funny."
And Fickman also recalled Pitch Perfect's Brittany Snow delivering a "really great" audition, though she'd end up landing the lead role in John Tucker Must Die, which filmed in Vancouver at the same time.
"Everybody was at the Sutton [hotel] and there was a lot of crossover," he said. "So these two casts had a lot of fun together." Um, can we see that movie, please?!
Prior to being cast as Duke, Channing Tatum had just one major film credit to his name, a small role in 2005's Coach Carter. But it was clear to Fickman and the rest of the team that he was bound to become, well, Channing Tatum.
"We were towards the end of casting. We had an eye on somebody who was already kind of involved in a pilot. We were looking at everybody for that role and then he came in," Fickman said. "He walks in and you know, Channing was never a kid who was this polished Hollywood guy who had been acting since the age of three and came in with, like, a smoking jacket saying, 'Hello, here's my eight-page resume of everything I've done before I was 12.' He was not that kid. His charisma, which now the world knows in triplicate, was there from day one."
Fickman continued, "I clearly remember—and I think I still have it somewhere—on my casting sheet, as he was talking, I was writing in crazy scribbles, ‘Star…star…star.' I remember everyone else was crazy-scribbling 'Star.'"
Early on in the filmmaking process, Fickman said producers considered casting singer Jesse McCartney as Viola's twin brother Sebastian.
"You're trying to find an actor you can, somewhat, sell has similar bone structure and a somewhat similar look to Amanda," he explained. "Jesse had come up for discussion and we were doing a lot of photo comparisons and then we just got very lucky with James Kirk. I think we had a photo of James and a photo of Amanda that we had side by side, and we went, 'Oh!' We were able to luck out with James, but I do remember that was definitely a discussion [with Jesse]."
The hardest part of turning Bynes into Sebastian was finding the right wig for the star to sport "because Amanda was so adorable that a lot of times if you went a little too long with the hair it just looked like she had a pixie cut," Fickman explained. "We had to find that line between how do we still know that's Amanda and yet at the same time how do we make it feel like that is another character that she is playing?"
The hair department was "working around the clock" to find just the right wig, with Fickman estimating they tried dozens of looks before finding the right one.
Fickman also outlined the filming schedule to make sure Bynes had enough time to get into character depending on which role she was playing.
"You really wanted to give her the time to step into those shoes," he said. "so we really had to find that time in hair and makeup and wardrobe to allow her the opportunity to handle it."
While some of the other actors—including Robert Hoffman and Brandon Jay McLaren—had experience playing soccer, Bynes and Tatum had to practice with a coach for weeks in order to film the action scenes. "They really had to dig it in and how great they were able to pull it off," the director said of his leads.
And Fickman revealed Tatum practiced "every morning" before filming in order to prepare for Duke's impressive goal at the end of the movie.
"We had the double on stand-by and I think Channing had wanted to know how many takes he had. I think time-wise I was like, I can give you two takes and then the double's going in,'" Fickman detailed, "and that beautiful bicycle kick shot is all Channing, first-take. He had just worked so hard."
It was Tatum's work ethic that Fickman said made the actor truly stand out, explaining, "It wasn't just the comedic timing, which was so funny and he was never pushing it, and it wasn't him being such a great, lovely person—which he still is—it was that dedication."
While there were once rumors about a possible romance between Tatum and Bynes back in the day, Fickman said he "never saw, like, 'Oh that person is in love with this person,' or someone had a crush on so and so."
But he did go on to admit, "Everybody had a crush on Channing!"
"Everybody was just lovely to work with and I think that's what shows in the movie," Fickman continued. "I think movies where the chemistry is there, you can't fake that chemistry on screen."
Fickman joked that Jonathan Sadowski, who ultimately played Paul, Viola's best friend and hairstylist, "can do a one-man She's the Man show because he auditioned for every role in the movie."
"I wasn't having much luck with Paul and Jonathan just stepped out and certainly showed how creative he was in terms of auditioning," he added.
While Karen McCullah Lutz and Kirsten Smith delivered a hilarious script, the actors were encouraged to improvise. "We allowed the cast to play," Fickman said, adding that the actor who played the most was David Cross as principal Gold.
"I don't think any of it was on the paper," Fickman revealed. "David is just one of the all-time great comedic actors."
Another cast member who ad-libbed a lot of their one-liners was scene-stealer Emily Perkins as Eunice Bates, Illyria Prep's eccentric student.
"Emily just said stuff that you'd just look at the script and look up at Emily and then look back at the script and then say, 'Yes, go with that!'" Fickman recalled with a laugh. "She had that big mouth guard, retainer in, so sometimes we'd be like, 'We're not sure what you're saying, so just say that!'"
Because they were filming in Vancouver, the cast and crew all stayed in the same hotel, "So on weekends we really tried to keep everybody together," Fickman said. He went on to share one of his favorite memories of the cast going to see Mr. and Mrs. Smith in theaters when an unexpected advertisement played before the film.
"So, all of a sudden, a Mountain Dew commercial comes on that had Channing in it and we are with the guy in the Mountain Dew commercial!" he recalled. "And we're looking and we had just exploded, we were the loudest…I think it was probably one of the first times Channing saw himself on the big screen like that."
Fickman looks back on the experience of filming She's the Man fondly, saying, "It was such a special movie. Anything you make in life can be hard, any job you have moments of good and bad, but that job was just a really great, joyful experience in terms of every day working with that cast and crew."
When Fickman first started dating his wife Kristen Gura Fickman, she had told him that She's the Man was her favorite movie, "which I thought was just a great pickup line. And then it was confirmed by her best friend that all they did was watch the movie and quote the lines to this day."
In fact, she might just know the movie better than he does, with Fickman continuing, "Every once in a while someone will call me or there will be some She's the Man trivia, something will happen, and I'm thinking, 'Wait, was that the line?' And my wife will step out and be like, 'Are you kidding me right now? Of course, this is actually how the line was said!'"
At the time of its release in 2006, Fickman admitted to being a little disappointed because "you're so driven by the box office...when we came out, we were like, 'Oh, OK, we did alright.' I think when we won the Teen Choice Surfboard for Best Comedy, I think that was a big moment where we were all like, 'That's cool. People did see our movie!'"
But the "cult following," he said, She's the Man has built since its release has completely altered his perspective.
"Now I think I'm feeling in retrospect what I had wanted to feel when we opened," Fickman admitted. "Like, 'Oh, we're not going to be the biggest movie ever made? Oh OK.' But now, new generations are seeing it and every time I work with a new generation of actors, younger actors will come up and say to me, 'I just saw She's the Man. Dude, that is funny!' I'm like, 'Wow, alright!'"
But, he continued, "Given all due respect, it was about 1602 when Shakespeare wrote Twelfth Night and that held up pretty well. So I figure that if Shakespeare was able to survive from the 1600s with our inspiration, surviving 15 years with She's the Man, we've got a long way to go!"