Following his breakthrough role as Robbie Ferrier in the blockbuster War of the Worlds (2005), Chatwin headlined studio films such as The Invisible (2007) and Dragonball Evolution (2009), an action-adventure feature based on the manga series Dragon Ball.

[13] Prior to this, he lived for a month in a travel trailer with a friend, stating, "We didn't have girlfriends; we were reading Kerouac and Ginsberg, driving up to the desert, walking in the dunes, and showering at 24 Hour Fitness.

[21] Chatwin was chosen out of several young actors to play Tom Cruise's rebellious adolescent son in the alien invasion film War of the Worlds (2005), directed by Steven Spielberg, based on the 1898 novel by H. G.

[24] Mick LaSalle of the San Francisco Chronicle considered the film "meticulously detailed and expertly paced and photographed",[25] Roger Ebert however called it "just a big, clunky movie containing some sensational sights but lacking the zest and joyous energy we expect from Spielberg".

Arie Posin's directorial debut about a group of superficial parents and young adults living a seemingly perfect life, had the world premiere at the Sundance Film Festival on January 25,[28] and was released theatrically on August 5, earning $351,401 on a production budget of $10 million.

[29][30] The film was poorly received by critics; writing for Rolling Stone, Peter Travers opined that it was "an appallingly clumsy and stupid take on drugs, kidnapping and suicide in suburbia".

Following a dysfunctional family whose mother goes missing then suddenly reappears claiming that she was abducted by aliens, Chatwin stars as Jeremy Cleary, the eccentric, but intelligent 16-year-old son of Michael (Reed Birney) and Bridget (Elizabeth Marvel).

[44] Chatwin starred opposite Anton Yelchin and Eva Amurri in the coming-of-age drama Middle of Nowhere directed by John Stockwell,[45] which premiered at the 2008 Toronto International Film Festival,[46] followed by a straight-to-DVD release two years later.

[49][50] The feature was critically panned upon release, Ross Miller of the Screen Rant calling it "a badly written film with horrible dialogue, lackluster action and a sense of fun that's nowhere to be found".

[53] In the same year, Chatwin teamed up again with Jamie Wollrab for John Markland's three-person play Red Light Winter at the Dairy Arts Center, during Boulder International Fringe Festival.

[54][55] In December 2009, Chatwin was filming the Showtime pilot Shameless, an adaptation of Paul Abbott's British series of the same name, starring alongside William H. Macy and Emmy Rossum.

[56] The 12-episode first season began airing in January 2011,[57][58] and over the course of three years, Chatwin portrayed Jimmy Lishman / Steve Wilton, Rossum's love interest, a car thief who comes from a wealthy family.

[60] The show received mostly positive reviews; Eric Goldman of IGN opined that Chatwin brings "the right vibe of scruffy determination" to his role,[61] while another critic noticed his "very intense and intimate chemistry" with Rossum.

[62] During an interview, when asked about one of the most controversial aspects of the series, the significant amount of nudity and sex scenes, Chatwin said: One of the things that attracted me to the project in the first place was getting past my own psychological barriers of being naked in front of people.

[66][67] In 2013, Chatwin guest-starred in the fourth season of The Listener,[68] and appeared in Isolated, a documentary narrated and executive produced by Ryan Phillippe about a group of surfers in search of untouched waves.

[76] The Hollywood Reporter's Leslie Felperin gave the film a negative review, describing it as "disappointingly bland", lacking any "metaphor, playfulness" and "enigmatic, magical-realism" necessary to sustain the offbeat premise.

[77] In 2015, Chatwin also portrayed a troubled man desperate to retrieve his bike in the short film The Cycle,[78] and recorded the audio version of Celeritas, a screenplay who featured on 2014 Black List.

[79] Chatwin starred as a detective tracking down a mysterious race of creatures in the TNT pilot Breed (2015),[80][81] and also that year, he secured a recurring role in the third season of Orphan Black, playing opposite Tatiana Maslany and Kristian Bruun.

[82] The following year, Chatwin landed the role of cartoonist Cameron Hawthorne in the CBS summer series American Gothic, which centers upon a white-collar family dealing with a serial killer.

[93] The romantic comedy Unleashed, written and directed by Finn Taylor, stars Kate Micucci as a woman whose cat and dog are transformed into men (Chatwin and Steve Howey).

[102] Also that year, he appeared in three films, starting with a cameo as Vincent D'Onofrio's drug-addicted son in the action-comedy CHiPs, directed by Dax Shepard, based on the television series of the same name.

Chatwin then portrayed modern-day cowboy Hugh Jay Linder in Blake Robbins' western noir The Scent of Rain and Lightning, based on the 2010 novel of the same name by Nancy Pickard.

[111] Chatwin also featured as a hedonistic bartender named Andy in the ensemble coming-of-age drama Summer Night (2019), directed by Joseph Cross in his directorial debut.

[116][117] Chatwin co-starred opposite Diego Boneta, Alexandra Daddario and Travis Fimmel in the romantic crime film Die in a Gunfight (2021), which has been described as a modern-day version of William Shakespeare's Romeo and Juliet.

Five years later, and a full blown obsession under my belt, I'm back in Italy standing at the epic Ducati factory", adding, "A perfect day for me is when I wake up and know that all I have to do is ride my motorcycle for the next ten hours in a particular direction".

[129] In order to learn more and improve his skills, in November 2016, over the course of one weekend, Chatwin attended the Keith Code's California Superbike School, alongside actor Nicholas Hoult, motorcycle journalist Sean MacDonald, singer and music producer Albert Hammond Jr. and entrepreneur Jesse Waits.

Chatwin took part at the BMX Boxer Cup challenge against former professional freestyle motocross racer Andy Bell, custom builder Maxwell Hazan and seasoned photographer Preston Burroughs.

[132] Chatwin is also part of WLF Enduro, a community of people from different backgrounds of work, such as teachers, salesmen or construction workers, brought together to ride 200 miles (320 km) in two days every year, throughout Southern California.

From Santiago to Ecuador and Bariloche, Chatwin and Markovina visit sacred places and meet interesting people, including indigenous rights activist Nina Gualinga.

Riding across Central America, the goal was raising money in order to purchase and install clean-water filters for the communities living in Honduras, Guatemala, El Salvador and Nicaragua.