Guillermo Diaz on working with Britney Spears, intense Scandal scenes, the upcoming Bros, and more

Fresh (1994)

Diaz's career kicked off with the movie Fresh, which centers on a boy who tries to create a better life for him and his drug-addicted sister inspired by the chess lesson his father taught him. In the movie, Diaz plays a character named Spike, but before landing that character he auditioned for three larger roles. "That movie got me into the SAG actor's union, which is a big deal for an actor," he shares.

An amazing opportunity, no doubt, but he remembers one unpleasant memory from filming during a sweltering New York City summer, when he was getting his considerably long hair blow dried. "I don't know why that sticks out, but yeah, blow drying my hair and feeling the intense heat on my scalp," Diaz recalls.

Party Girl (1995)

Diaz remembers how much fun he had working with one specific castmate. "Parker Posey just made that movie so special for me," he says. During the audition process he went in five times, doing the last couple with Posey, who he calls "the most unique person" he's ever met. "I remember walking into the audition, getting to pages with my lines, and she was like 'Let's put that shit down. Let's just do it.' We just [improvised] together," he recalls. Diaz adds that she that brought a singular perspective to Party Girl, like many of her other roles, and most of her wardrobe was her own.

As a self-described "nerd," Diaz wasn't hitting clubs in the Big Apple in the '90s, but he says Posey would take him out on the town. For clubs like The Tunnel, you had to get chosen to go in, and with Posey he'd get right in.

Stonewall (1995)

For a number of reasons, Diaz says Stonewall was a very special film for him. Inspired by the memoir of gay historian Martin Duberman, the 1996 film is a fictionalized account of the weeks leading up to the Stonewall riots. It centers a young gay man named Matty Dean (Frederick Weller), Diaz's La Miranda, and her friends who take him to the Stonewall Inn.

Diaz credits hair stylist and makeup artist Jason Rail for helping transform him into La Miranda, who's in drag throughout the movie. "I wasn't out of the closet at the time, so it was very trippy playing this lead character who was very out and open," he shares, adding that playing La Miranda made him feel more confident about his own sexuality.

Half Baked (1998)

From Diaz's Half Baked audition for Scarface, you would have never guess it was a stoner comedy. The scene he auditioned with was one where his character was burying someone, so he played it as if it were a dramatic movie. "I guess it worked because I got the role," he says, starring opposite Dave Chappelle in the 1998 film about four lifelong friends.

Diaz has fond memories of filming the movie in Toronto, including working with director Tamra Davis. He even got to hang out with her then husband, Beastie Boys' founding member Mike D, who Diaz is a big fan of. "I started acting when I did a talent show in high school and I played Mike D where we did a medley of songs," he recalls.

Weeds (2007-2012)

The first thing Diaz remembers about Weeds is that he was only supposed to in four episodes. "It sort of just happened. They kept adding me to episodes, so I didn't even have time to think about it," he recalls. His character, also named Guillermo, appeared in 20 episodes across five seasons starring in season 3.

The actor only has positive memories of working with lead Mary Louise Parker, who he found supportive and encouraging. "She's an icon and I was like submissive to her, but then on screen I had to be aggressive and dominant towards her, so that was a trip, but we had a blast doing it," Diaz says about his stint as Guillermo Garcia Gomez.

Britney Spears' "I Wanna Go" music video (2011)

"I was supposed to be in the beginning of the video where she says my line from Half Baked then she points to me and I give her a thumbs up," Diaz says about the initial plan for the pop princess' "I Wanna Go" video. But a few days before the shoot, someone dropped out and Diaz suddenly found himself with a bigger role, driving around with Spears and pouring milk on himself.

Diaz remembers Spears and kind and powerful, and, while she was shy in between takes, she came to life when the camera started rolling. "I'm so proud to be part of something with Britney Spears because I just love her and it was such an awesome moment in my life," he says.

He even has a sourvenir from the experience: "I remember driving home after the shoot in my milk-soaked pants because they let me keep the jeans."

Scandal (2012-2018)

Two words: fart noises. Scandal was a series full of brutal twists and dark moments, so it's no surprise that the cast needed to find levity, and fart sounds one was of the ways they did it. "Scott Foley started this thing where he does this noise with his mouth and then we all started doing it," Diaz recalls, adding that even the crew would get in on it.

Over the course of seven season, Diaz had some intense scenes as assassin-turned-tech-guy Huck, one where he was waterboarded. "We had to do all these rehearsals of how they were going to waterboard me and pour the water on my face upside down, and it was intense," he shares. In another, Huck was trapped in the trunk of a car that was pushed into a quarry lake. Diaz spent two weeks training for the episode — learning under-water exercises and holding his breath in his full costume — which then took some 10 days to film. "I would come to set and they would just spray me down with water," he recalls.

Girls (2016)

Diaz first met Girls creator Lena Dunham when she guest starred on Scandal, where Huck actually kills Dunham's character. He recalls the scene having a lot of blood and the pair doing a whole photo shoot after the death scene.

On her HBO comedy, Diaz guest starred as a stranger who picks up Dunham's Hannah on the side of the road. "I'm so proud to have been on a show that was so groundbreaking. I'm a huge fan of Lena Dunham, she's so brilliant," he says. "I was so elated and freakin' psyched." Like their time together on Scandal, Diaz says there was a lot of laughter on the very positive and welcoming set of Girls.

Broad City (2019)

It all started with the White House Correspondents' Dinner. Diaz and his Scandal costar Katie Lowes met Broad City creators Ilana Glazer and Abbi Jacobson at the Vanity Fair party for the event, where they bonded over loving one another's shows.

Shortly after, Diaz's people got a call and he was playing Johnny, Jaimé's (Arturo Castro) boyfriend. "I did come in very nervous because this was one of my favorite shows, but we had a f---ing blast doing it," he says. He even got to see Glazer's work as a director on set. "Those girls are crazy. They do whatever the f--- they want. I loved it," he adds.

High Maintenance (2019)

High Maintenance is now one of Diaz's favorite TV shows, but he's happy he had never seen it when he was offered a role on it. "I would have been a lot more nervous and freak out. When you're a fan of something there's pressure to do a good job, but I was more chill," he explains. In the episode, he and Rosie Perez play an eccentric couple who meet Ben Sinclair's The Guy on the street as they're out with their fake baby (a proxy infant). Diaz remembers meeting Sinclair his first day on set and not knowing he was the star and creator. "He was a nice, cool guy," Diaz recalls.

United We Fall (2020)

Diaz had worked in front of a live audience since the short-lived House of Buggin' starring John Leguizamo. But ABC's United We Fall changed that, and Diaz admits being nervous to film the sitcom about a couple (Will Sasso and Christina Vidal) and their two young kids, the husband's live-in mother (Jane Curtin), and the wife's brother (Diaz). "I was shooting something in New York and had to fly into L.A. and rehearse for like a day before we started shooting — it all happened so quickly," he shares.

Playing Chuy was made easier because of his effortless chemistry with Vidal, who played his sister Jo. "We hit it off right away," he says, adding that he's also good friend with her sister, Lisa. "We both grew up in New York, so we bonded super quick. We started teasing each other right away."

Law & Order: Organized Crime (2021-present)

Law & Order: Organized Crime isn't Diaz's first stint in the crime-fighting franchise; he appeared twice on both Law & Order and Law & Order: Special Victims Unit before landing his recurring role on the Christopher Meloni-starring series as Sergeant Bill Brewster. "I love working with the Law & Order family. That universe is just really great," he says about entering a well-oiled machine in season 2.

While Diaz sometimes prefers to audition, Sgt. Brewster was offered to him. "It doesn't happen often, but the few times they don't want me to audition is because they're sure they want me for the role," he explains.

Bros (2022)

Diaz plays one half of a straight couple alongside Monica Raymund in Bros, written by and starring Billy Eichner. "Billy's really enthusiastic. Watching him was like taking a masterclass in comedy — he's just out of this world and he's such a perfectionist," he says, "I have a small role in it, but I'm still so extremely proud to be part of it."

In addition to thinking it's a great film, Diaz looks back on the project as an incredibly special one: Not only were all the LGBTQ roles played by queer actors, but so were the straight roles, like his. Being on a set with all LGBTQ+ actors is an experience Diaz looks back on with pride. "It's really nice to be on set and see this authenticity," he says.