Community Issue: Harrison Osterfield

We nip to the pub for a pint and a pie with the star of the hit Netflix show 'The Irregulars'.

Harrison wears jumper and blazer by GOLDSMITH VINTAGE.

This spring the world properly got to know Harrison Osterfield thanks to his role as Leopold in the new Netflix series The Irregulars, based on Sir Arthur Conan Doyle’s Sherlock Holmes books. But while many may already know the 25-year-old actor as the best friend and former assistant of Tom Holland, he has been working towards this moment since he was a teenager.

Osterfield, who admits he was very shy as a child, found freedom acting in the plays put on at his strict boarding school. From there, he enrolled at the BRIT School, the performing arts institution that counts Adele, Amy Winehouse and underrated pop princess Leona Lewis among its alumni. For Osterfield it was like walking into Fame: The Musical – he found himself surrounded by passionate, larger-than-life personalities who were determined to make it in the industry.

Harrison wears jumper by GOLDSMITH VINTAGE, shorts by LOU DALTON, shoes and socks Harrison’s own.

“When I got the call for the role I was just screaming. It was a big moment for me”

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It was at the BRIT School that he met Holland, and they quickly became close friends. After continuing his studies at the London Academy of Music and Dramatic Art, Osterfield received an offer he couldn’t refuse from his best pal. “It was pretty amazing. I came out of drama school and Tom was going to do this huge movie [Spider-Man: Homecoming] in Atlanta and he said, ‘They’ve said I can bring someone along, do you want to come?’ And I was like, ‘Absolutely, let’s go.’” Not only did Osterfield work as Holland’s assistant, he was an extra in Spider-Man: Homecoming and Avengers: Infinity War. “It was an amazing experience to see how these bigger, CGI films worked,” Osterfield says.

Osterfield has the utmost admiration for his friend and former Spider-boss. “He’s a very hard worker, and the enthusiasm that he puts into the job and how personable he is with the crew was a real learning experience for me,” he says. “And it just made me want it more. We spent a year and a half working together. In that time, I gathered contacts, gathered confidence, and really made a leap of faith. I said to him, ‘Listen, mate, I’m going to try to make a go of this and see what happens.’ And I think if I hadn’t taken that leap of faith, I wouldn’t be here today.”

Harrison wears jacket and coat by DANIEL W. FLETCHER, T-shirt by DIOR and trousers by SANDRO.

Osterfield had already appeared in several short films, including 2018’s Vent, about a couple trapped in their home in a pandemic, but it was his role as newly enlisted soldier Snowden in 2019’s Golden Globe-nominated show Catch-22 that really drew the industry’s attention. George Clooney directed, produced and starred in the series. “I did a self-tape for it. And he said, ‘That’s the guy, I want him,’” Osterfield recalls. “It was my first professional  job on set. [I was] flown out to Sardinia and met George there.” According to Osterfield, his grandmother was almost more excited about him working with Clooney than he was, and the Oscar winner gave the budding star words of reinforcement and wisdom that have stayed with him, though he remains tight-lipped about the specifics.

In The Irregulars, Osterfield plays Leopold, an intelligent and charming addition to a misfit gang that roams the streets of Victorian London, helping John Watson solve crimes and search for Sherlock himself. His character is based on Prince Leopold, the youngest son of Queen Victoria, who suffered from haemophilia, although the mystery-solving is all fictional. “It’s a new thing for me, playing a real person,” Osterfield says. “The fact that [I could] research about this character and see how Queen Victoria was so protective about him, and the fact that his [teachers] noticed how intelligent he was at a young age, these were really useful tools and information to use. I’ve channelled all of that.”

Harrison wears jumper by GOLDSMITH VINTAGE.

“Tom Holland is a very hard worker, the enthusiasm he puts into the job and how personable he is with the crew was a real learning experience for me”

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The Irregulars isn’t your average Sherlock Holmes remake. This time, Sherlock takes a back seat and it’s the ragtag gang of “irregulars” who are front and centre of the plot. “I had five auditions for it that went on for over two months. It was a very long process,” Osterfield continues. After each audition, his hunger for the role grew. “When I got the call for the role, I was just screaming. It was a big moment for me.”

Taking on a story that is almost 130 years old is daunting, but Osterfield was more than up for the challenge. He admits that he hadn’t been the biggest Sherlock fan beforehand, but he took on the role with a fresh perspective. “I saw the Robert Downey Jr films and loved them. But I made a decision when I got the part – my character was basically going to be experiencing London for the first time in that world [because of the sheltered life he had lived], so I thought, ‘Maybe I’ll do that as well and go and work as [though I’m] a blank slate and learn as the character lands at the same time.’ So I treated the scripts as a bible,” Osterfield says. The series started shooting in Liverpool at the end of 2019, but production was halted the following March, two weeksbefore it was due to wrap, because of the pandemic. It wasn’t until August that it was able to resume.

Harrison wears jumper by TOD’S and blazer by KENZO.

“It’s obviously a very different Sherlock Holmes [from what we’ve seen] before,” Osterfield says. “The fact that he is at his lowest ebb. He’s not as brilliant as he once was. He’s not able to solve the cases that he wants the kids to [help with], and that’s going to flip the genre on its head, but I think [people] are going to be surprised by how much material is in this show. I mean, there are so many different genres in it.”

Teen dramas sometimes struggle to portray authentic diverse friendship groups but The Irregulars feels different and it’s refreshing. “They did an amazing job casting the right people for the right roles, regardless of background, ethnicity or anything like that,” Osterfield says. “The female leader [Bea, played by Thaddea Graham] in the gang is very important. The industry needs to keep growing and telling these stories.”

While there’s no official news yet about a second series, the actor is eager to keep the ball rolling. “I’d love to continue exploring this character. I think the series does a great job of wrapping things up while also leaving it quite open-ended. And there’s definitely scope to do so much more exploration of these characters.” Our fingers are firmly crossed for season two, but whatever happens, we’re confident we’ll be seeing a lot more of Osterfield on our screens in the future.


The Irregulars is available to stream on Netflix.

  • Photographer Emmanuel Owusu-Afram
  • Writer Trey Gaskin
  • Stylist Kamran Rajput
  • Creative Director Julia Salotti
  • Groomer Davide Barbieri at Caren Agency using DERMALOGICA
  • Set Designer Marco Turcich
  • Producer Grace Finger
  • Photography Assistants Doma Dovgialo, Chloe Burgess and Jed Barnes

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