Red Velvet, Tricycle, London Damned by Despair, NT Olivier, London Loserville, Garrick, London

On 25 March 1833, the crowd flocking into Covent Garden's Theatre Royal doubtless expected a tour de force from Edmund Kean, popularly deemed the greatest actor of his time. Coleridge observed, famously, that to see him act was "like reading Shakespeare by flashes of lightning", yet the shock reverberating round the auditorium that day in March was of a different ilk. Playing Othello (blacked-up, as was customary), the 46-year-old Kean faltered, cried out "I am dying", and collapsed on stage. He did not live to see the summer.

As Lolita Chakrabarti's new play Red Velvet points up, the really stunning development, however, was the hiring of an African-American actor, Ira Aldridge, to step into Kean's revered shoes – even as British society was riven over the pending Abolition of Slavery Act.

Red Velvet is a fascinating portrait of Aldridge, played here by Adrian Lester on riveting form. Combining historical research and imagination, the biodrama envisages the racial tensions escalating backstage after the progressive theatre manager, Pierre Laporte (Eugene O'Hare), casts his non-Caucasian buddy and dismisses all objections. Lester's Ira plunges into rehearsing his scenes with Desdemona – Charlotte Lucas's Ellen Tree – pushing for more heartfelt feeling and physical contact. The more reactionary members of the company and of the press are outraged – not least Kean's son, Charles (Ryan Kiggell), who is Tree's fiancé.

For sure, Chakrabarti has a great deal to pack in in terms of expositional background and an outline of Aldridge's later years of acclaim in continental Europe. Conceivably, in a lesser production, Red Velvet might feel wooden. But Indhu Rubasingham's superb ensemble grasp that every argument – ethical, political, and aesthetic – is driven by complex personal motivations. Thus history springs into startlingly vigorous life.

The production is beautifully staged, in period costume, on bare wooden boards thrusting out from a battered gold proscenium arch (design by Tom Piper). There are also witty transitions between the formal, pose-striking style of 19th-century acting and warm-blooded naturalism.

Glancing from under auburn ringlets, Lucas's transition from diva-ish froideur to artistic flexibility comes with proto-feminist humour and a faint hint of infidelity. She's supported by outstanding cameos from Natasha Gordon as the deceptively meek Jamaican maidservant, Connie, and newcomer Rachel Finnegan who plays multiple roles with consummate assurance. O'Hare's commercially compromised showdown with Lester is desperately agonised and admonishing too. No one is, morally, black or white. Lester's Ira is electrifying and multilayered, charismatic and loving but also, possibly, a womaniser, hardening into a lonely, bitter egoist.

This is a terrific kick-off for Rubasingham's artistic directorship at the Tricycle, and Lester's prowling, leonine Othello should compare intriguingly with his forthcoming National Theatre performance, in the same role, scheduled for 2013.

Meanwhile, Damned by Despair – a shocking NT flop – merely makes one want to launch oneself despondently off a cliff. But the villainous desperado Enrico pips you to the post in Tirso de Molina's 17th-century morality play. Enrico nosedives into the ocean, only to be saved by God's mercy, bestowed on this serial-killing thug because he has retained a smidgeon of faith. Meanwhile, the long-devout hermit Paulo is conned by the devil into thinking he is irredeemably damned – and therefore he is.

It's not only difficult to comprehend this kind of divine justice, it is also hard to believe quite how bad Bijan Sheibani's underdirected production is, combining some of the lamest acting I've seen this year, a stylistically lurching translation by Frank McGuinness, and largely pointless modern-day costumes. Sebastian Armesto's scruffy Paulo adopts a superficially fevered manner while Bertie Carvel's Enrico, rattling through his lines, sounds about as scary as Larry Grayson. Amanda Lawrence, with her ashen face, makes a creepy Satan. However, designer Giles Cadle's mountainscape is so ill-lit that most of the cast are acting in the dark. No insightful lightning bolts here.

Lastly, in Loserville, a "Eureka" lightbulb is surely going to ping on above Michael Dork's head. Supposedly it's 1971 and he's an American high-school geek (played by Aaron Sidwell), about to invent email with the help of his brainy sweetheart, Holly. I'd like to think some clever teenagers will be heartened by this bully-defeating romcom, co-written by Elliot Davis and James Bourne (of the band Busted). However, you'd have to have a mental age of about six to think this wasn't dumbed-down, formulaic pap, drawing on Grease, Glee and High School Musical.

Designer Francis O'Connor has fun with fast-changing cartoon settings, using giant spiral notepads. I liked the feisty girls in choreographer Nick Winston's arm-whirling chorus line, and Eliza Hope Bennett's Holly shines when she's granted a tiny solo, but the nerdy boys are wearisome and most of the songs are thudders.

'Red Velvet' (020-7328 1000) to 24 Nov; 'Damned by Despair' (020-7452 3000) to 17 Dec; 'Loserville' (0844 412 4662) booking to 2 Mar 2013

Cheek by Jowl is touring John Ford's sibling-incest tragedy 'Tis Pity She's a Whore. Electrifying, darkly funny and poignant, it's at Bristol's newly reopened Old Vic (Wed to 3 Nov). The NT's comic hit One Man, Two Guvnors is on tour too, with Rufus Hound and Jodie Prenger, starting at the Curve Theatre, Leicester (Thu to 3 Nov).