He is best known for his roles in the series The Pillars of the Earth, The Borgias, The White Queen, Victoria, Vikings: Valhalla, and for his discursive Natural History podcast, Trees A Crowd.

[6] In 2006, Oakes performed a 90-minute abridged version of Much Ado About Nothing as part of the Royal Shakespeare Company's "Complete Works" festival along with his final year graduates from the Bristol Old Vic Theatre School.

[7] Oakes was present to accept the Jury Prize at the 2011 Romy Awards in Vienna alongside Donald Sutherland and Natalia Wörner.

[citation needed] Other performances between 2008 and 2013 for "Read Not Dead" include an early quarto edition of Henry IV: Part One as Prince Hal opposite Benjamin Whitrow's Falstaff, Calderon's Life is a Dream (La Vida Es Sueno) as Segismundo, Taming Of A Shrew as Aurelias, The Spanish Tragedy as Lorenzo, The Return from Parnassus as Ingenioso, Bassianus as Geta, Gorboduc as a "smooth, almost oily"[10] Arostus, John Lyly's Love's Metamorphosis as Montanus, and Thomas Middleton's Your Five Gallants as Tailby.

[11] In a return to TV period dramas in 2015, Oakes guest-starred in both the third season of Endeavour with Shaun Evans and in BBC's limited series The Living and the Dead with Colin Morgan.

In 2017, Oakes starred in the film adaptation of Albert Sánchez Piñol's novel Cold Skin, directed by Xavier Gens and co-starring Ray Stevenson and Aura Garrido.

He also starred as Thomas Novachek in the London West End premiere of David Ives's play Venus in Fur at the Theatre Royal Haymarket.

The event was overseen by High Court Judge Sir Michael Burton; the QCs were John Kelsey-Fry, Jonathan Laidlaw, Dinah Rose, and Ian Winter, and the foreman of the jury was Jeremy Paxman.

"[19] While at university, Oakes directed numerous plays including Martin McDonagh's Beauty Queen of Leenane, Harold Pinter's The Dumb Waiter and Anthony Minghella's Whale Music.

Later that year, Oakes once again turned to literary adaptation, taking a production of Stephen King's The Boogeyman to the Edinburgh Festival Fringe.

[20] With his and Bell's theatre company, Dog Ate Cake, in 2009 Oakes directed a small tour revival of John Maddison Morton's Box and Cox.

[23] Oakes recently directed an extract of Robert Daborne's A Christian Turn'd Turk as part of a special "Read Not Dead" event at Shakespeare's Globe.

Winning the event, teamed with Dr Emma Smith of Oxford University, Oakes directed the full play on Sunday 5 October 2014 in the Sam Wanamaker Playhouse.

In 2019, Oakes helped organise, and alongside Michael Palin, Twiggy and others, appeared in the "Just A Book" poster campaign on the London Underground.

[34] Writing in an editorial for the Sunday Times on 2 November 2019, Oakes said: Trees give us so much: if you can come up with a better technology and material that is cheap, enhances wellbeing, stimulates happy childhood memories, sequesters CO2, boosts biodiversity and even just looks as pretty as a copper beech, a hawthorn or a horse chestnut, then I’ll bow to you.