From Child Star to Gay Icon: Jonathan Bailey’s Best Roles to Date

Let’s start with the obvious: who among us doesn’t love Jonathan Bailey? The sexiest man of the year (scientifically, spiritually, emotionally), the reigning king of yearning on screen, and quite possibly the most charming British gay man alive. Many first discovered him through his star-making turn as Viscount Anthony Bridgerton in Bridgerton — where he basically delivered an entire semester’s worth of curriculum on “How to Long For Someone While Dripping Wet.” Others fell for him as Tim Laughlin in Fellow Travelers. And lately? Bailey has the girls, gays, and theys collectively shrieking even while he’s playing a scarecrow in Wicked and Wicked: For Good.

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But the actor has been dazzling audiences long before the corsets, emotional monologues, and straw-covered musical numbers. Our man has been acting for almost three decades — yes, receipts go back to 1995. So let’s take a delicious, cheeky journey through Bailey’s most iconic roles proving he’s been that guy all along.

@drinksforgayz

jonathan bailey being delectable and charming behind the scenes of CBBC leonardo 🫠😍 #gay #jonathanbailey #foryou #fyp #memes

♬ original sound – drinksforgayz


1997 — William Kilshaw in Bramwell

Tiny Bailey. Big talent. You could already sense he was destined for awards, standing ovations, and global thirsting with that cheeky smile and curious eyes.

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2004 — Cyril in Five Children and It

A magical sand fairy, chaotic CGI, and a young Jonathan being adorable? Peak childhood cinema.

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2007 — Caspar in St Trinians

Camp British chaos, iconic uniforms, and early queer-coded energy. Bailey fit right in.

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2011 — Flatpack in Campus

A short-lived comedy but Bailey delivered charm, timing, and face. It was his “yes I can be chaotic and gorgeous at the same time” era.

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2011–2012 — Leonardo da Vinci in Leonardo

Yes, he played Leonardo da Vinci. Yes, he had that boyish chari as a tennage Leonardo da Vince. Yes, he served.

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2012 — Alfie (in THAT gold dress) in Me and Mrs Jones

Let’s pause. The gold dress. The nonchalant pose. This wasn’t acting — this was a cultural reset for the gay community. 

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2012 — Tom in Groove High

A young Jonathan as a teenage rock star juggling fame and school? Charisma louder than the soundtrack.

@troicksofficialson

Young Jonny is so cute, Tom is one of my favourite characters | @ryen @𝘑𝘶𝘭𝘪𝘦𝘵𑁍 | #groovehigh #jonathanbailey #jonathanbaileyedit #fellowtravelers #wicked

♬ original sound – Troicks Son‼️


2013–2015 — Olly Stevens in Broadchurch

The actor was giving local investigative journalist realness with an intensity and soft emotional devastation that left many others remembering his character…and forgetting that the man who is now ruling Hollywood was once a local journalist (well, on screen). 

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2014 — Psi in Doctor Who

A psychic hacker in the Whoniverse. Representation matters.

@jessicawaiter

Knew I thought this guest star was both familiar and very very attractive… #wicked #wickedmovie #jonathanbailey #fiyero #doctorwho #doctorwhotiktok

♬ original sound – jessicawaiter


2016 — Jamie in The Last Five Years & Sam in Crashing

A double-hit era: powerhouse musical vocals and frosted blonde tips in a messy flat-share comedy. The range was unbelievable.

@ericadanlle

video by Musical Sparks on YouTube #jonathanbailey #musicals #theatre #fiyero #wicked

♬ original sound – erica


2017 — Ash in Chewing Gum

A comedic gem in a chaotic masterpiece of a show. Bailey understood the assignment.

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2018–2019 — Jamie in Company

His Olivier Award–winning moment. A West End king was officially crowned.

@yeehaw2709

vid cred: aurora spiderwoman on yt #jonathanbailey #wicked #wickedthemusical #company #westend #broadway #broadwaymusicals #theater #theaterkid #theatertiktok

♬ original sound – yeehaw


2019 — Lance Miller in Tom Clancy’s Jack Ryan

Suddenly Bailey in a political-action thriller? It’s giving “dangerously attractive with classified information.”

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2020–Present — Viscount Anthony Bridgerton in Bridgerton

This role launched a global obsession. The yearning. The tension. The smolder. The lake scene. Bailey carried Season 2 like it weighed nothing.

@benniedct

I’m STARING 👀 thanks for all the love on my Daphmon edit!! 🫶🫶 scp: aeunqiascenes cc: mine sharpen: impvlse #anthonybridgerton #anthonybridgertonedit #jonathanbailey #jonathanbaileyedit #bridgerton #bridgertonedit #bridgertonseason2 #bridgertonscandal #fyp #fyppp #foryoupagе #edit #edits #viral #xyzbca #aestheticedits #aftereffectsedit

♬ original sound – ʙᴇɴɴɪᴇᴅᴄᴛ


2023 — Tim Laughlin in Fellow Travelers

Devastating, moving, romantic. A performance that had viewers emotionally ruined in the best way possible.

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RELATED: Jonathan Bailey Talks Prosthetic Penises and Steamy Scenes


2024-2025 — Fiyero & The Scarecrow in Wicked / Wicked: For Good

Only the sexiest (gay) man alive could make blue pants, dancing, and straw sexy. History should record this.

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2025 — Richard II in Richard II

A Shakespearean turn filled with elegance, fragility, and power. The theater gays win again.

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2025 — Dr. Henry Loomis in Jurassic World: Rebirth

Dinosaurs, chaos, and Bailey running dramatically in a blockbuster? Cinema is saved.

@fandango

pookie looks STRESSED in #JurassicWorldRebirth 😩 #movietok #filmtok #jonathanbailey #jurassicpark #Jurassicworld

♬ SPORTS CAR x BUTTONS by Adamusic – Adamusic


The Legendary 32-Day Work Sprint

Bailey once filmed Fellow Travelers, Bridgerton, and Wicked within 32 consecutive days.

Zero days off. Airplane → 1960s cabin → airplane → Regency ballroom → airplane → choreography rehearsal → repeat. This is not a normal human schedule. This is talent, caffeine, jet lag, and pure gay determination.

@jonathanbaileystan

Jonathan rehearsing for Wicked! 😍🕺🏻 📹 @leahhill_dancer (check the full bts video on her account!) ❤️ #jonathanbailey #jonnybailey #jbayleaf #bridgerton #anthonybridgerton #netflix #fellowtravelers #skippy #timlaughlin #showtime #wickedmovie #wicked #Fiyero

♬ Dancing Through Life – Jonathan Bailey


Why We’re All Obsessed

Because Jonathan checks every single box, it’s almost unfair at this point. He’s devastatingly talented in every role he touches, carrying the kind of West End excellence that only comes from years of hard-earned craft. He’s ballet-trained, which explains the effortless grace he brings both onstage and onscreen, yet he remains genuinely humble despite the global attention. Add in the fact that he’s dangerously handsome and consistently delivers fan interactions worthy of sainthood, and it becomes clear why audiences can’t stop talking about him.

Jonathan isn’t just a star. He’s a cultural era. And the gays? We’re absolutely, permanently, blissfully seated.

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