He is best known for playing the lead in Stephen Poliakoff's BBC films Joe's Palace and Capturing Mary, and also for appearing in Dominic Cooke's 2021 National Theatre revival of The Normal Heart, for which he was nominated for an Olivier Award for Best Supporting Actor.

While at the London Academy of Music and Dramatic Art, Wynter ushered at the Royal Court theatre, a job which he left to make his professional debut in[3] Stephen Poliakoff's 2007 BBC/HBO films Joe's Palace and Capturing Mary.

His other work for the company includes[4] Henry IV Part I and II, opposite Roger Allam, and new plays The Frontline by Che Walker and Bedlam by Nell Leyshon.

[5] The play, revolving around an out of work London actor in love with his married friend, the star of a Hollywood superhero franchise, was described by The Independent as a "funny and unflinching exploration of black masculinity".

[6] In January 2014, after responding to a trailer for a new season of TV drama which failed to include a single BAME artist, Wynter brought together a group of friends and colleagues, actresses Ruth Wilson and Stephanie Street, actor and director Daniel Evans, casting director Andy Pryor and actors Malcolm Sinclair and Kobna Holdbrook-Smith, to send out the message that the UK arts must reflect everyone regardless of race, gender, class, sexual orientation or disability.