After auditioning for
Crawford Productions, Herriman was cast as Frank Errol in drama series
The Sullivans at the age of ten. The role lasted over a period of two years and saw him nominated for three
Logie Awards, including
Most Popular New Talent and Best Performance by a Juvenile. and
For The Term of His Natural Life (1983), an adaptation of
Marcus Clarke's 1894 novel, featuring
Colin Friels. He also had a role in
Grundy's soap opera
Taurus Rising. before being cast as Mark Jorgensen, the bespectacled best friend of
Ben Mendelsohn's Danny Clark in his first feature, the Australian cult comedy classic
The Big Steal (1990). When his appearance in
The Big Steal didn't lead to further film work, Herriman began scripts and plays, including
Soar. He took his play to newly-formed theatre group,
Tamarama Rock Surfers, gaining the attention of other creative up-and-comers including
Joel and
Nash Edgerton. Intent on acting and writing full time, he quit his insurance job at the age of 27 and made two short films, the
Tropfest finalists
They and
The Date. Over the next couple of years, Herriman had guest roles in American and Australian series alike, including
The Loop,
Cold Case,
Chandon Pictures,
CSI: Crime Scene Investigation,
Satisfaction,
Offspring and
Rake. Herriman then landed his breakthrough role as redneck Dewey Crowe in crime drama series
Justified in 2010, going on to work on the show for six years. In 2012, Herriman co-starred as Reg in Australian comedy-horror film
100 Bloody Acres alongside
Angus Sampson before taking on another recurring role as hitman Mr. Jones on the
CBS crime series
Vegas. He also appeared as Ray, a member of the Cavendish gang in
Gore Verbinski's 2013 film
The Lone Ranger, opposite
Johnny Depp. In demand back in Australia, Herriman played the main role of titular bushranger in 2013
ABC telemovie,
The Outlaw Michael Howe. That same year, he was also a performer and contributing writer on the
ABC sketch comedy series ''
The Elegant Gentleman's Guide to Knife Fighting''. In 2014, he had a main role in
Josh Lawson's debut feature
The Little Death. He also played music executive
Chris Murphy in biographical miniseries
INXS: Never Tear Us Apart In 2015, Herriman appeared in the
CBS series
Battle Creek, played the homeless Romeo in
Starz miniseries
Flesh and Bone and also the violent hitman Buddy in the first season of the
HBO/
Cinemax series,
Quarry. In 2016, he appeared in Australian feature film
Down Under winning an
AACTA Award for Best Lead Actor in a Television Drama for his portrayal. He also played a role in 2018 Australian film,
The Nightingale. 2019 saw Herriman play
Charles Manson twice, beginning with an episode of crime series
Mindhunter, followed by
Quentin Tarantino's feature film
Once Upon a Time in Hollywood, with
Brad Pitt,
Leonardo DiCaprio and
Margot Robbie.
Nicholas Hammond (Freidrich from
The Sound of Music) who was also appearing in the film, had previously played Herriman's father in a stage production of
Lost in Yonkers in 1992. When he learned that Herriman was playing Manson in
Mindhunter, he put forth his name for the role of the cult leader in the film. After seeing Herrimann's name written down,
Timothy Olyphant, who'd played opposite him in
Justified also recommended him to Tarantino, leading to an audition that secured Herriman the role. Herriman had several other roles in 2019, including playing Paul Allen Brown in
Steven Conrad's neo-noir thriller series
Perpetual Grace, LTD, opposite
Ben Kingsley. He appeared as a menacing priest in Australian drama series
Lambs of God and had a role in climate change drama series
The Commons. He also featured in
Netflix crime miniseries
The Serpent as a boozy Australian diplomat, voiced the claymation character 'Street Hustler Boy' in stop-motion series
Ultra City Smiths and played against type, as a 'nice guy' in historical miniseries
The Underground Railroad, based on the
book of the same name. The following year, he played Captain Gaines in
Disney+ series
The Artful Dodger, a series designed aa a sequel to
Oliver Twist, following the titular character as he adjusts to his new life as a surgeon in Australia. He also had a supporting role in Australian psychological horror
Run Rabbit Run, opposite
Sarah Snook and played Brucie in American crime drama film
The Bikeriders with
Austin Butler and
Tom Hardy. In 2024, Herriman played British band manager
Nigel Martin-Smith in
Robbie Williams biopic
Better Man and Roger in Australian drama film
How to Make Gravy, inspired by the song by
Paul Kelly. The following year he had a supporting role in the body-horror film
Together, with
Dave Franco and
Alison Brie. He then starred in Australian director
Dario Russo's 2025 debut feature
The Fox, together with
Jai Courtney,
Emily Browning, and featuring the voices of
Sam Neill and
Olivia Colman. That same year he joined the main cast of American horror-comedy series
The Bondsman, alongside
Kevin Bacon, playing the role of crime mogul Lucky Callahan. In 2026, Herriman, together with
Richard Roxburgh and
Toby Schmitz embarked on a national Australian tour of
Yasmina Reza's comic play
Art, playing the role of Serge. Herriman is due to appear in upcoming American action thriller film
Subversion, alongside
Chris Hemsworth,
Lily James,
Michael Peña,
David Wenham and
Teresa Palmer. Herriman has also made acting appearances in music videos for
Bernard Fanning's “Wasting Time” (2016) and
Julia Stone's "Unreal" (2020). ==Personal life==