Dodger Lane (Peter Sellers) has it easy in prison thanks to a progressive Governor (Maurice Denham) who sees time spent inside as an opportunity to improve oneself, all the better to contribute to society when they are finally released. This offers Lane plenty of opportunity to pull the wool over his eyes, and those of the warders, and he shares his cell with two accomplices, safe cracking expert Jelly Knight (David Lodge) and the eager, less experienced Lennie Price (Bernard Cribbins). They wake up one morning to the milkman making his delivery to their cell (through the window) and Lennie's mum putting a song request on the radio, but they're about to get a real wake up call...
Peter Sellers never appeared in a Carry On film, but for the first half hour of Two Way Stretch, you could be forgiven for thinking you were watching Carry On Prison what with the risqué gags about the Governor's marrow, which he hopes to win an agricultural prize with. Scripted by Len Heath and John Warren (who contributed to another Sellers crime comedy favourite, The Wrong Arm of the Law), with additional dialogue by Alan Hackney (co-writer of I'm All Right Jack), the film was blessed with a superb array of British comic acting talent with the bonus of turning into a pretty innovative heist movie in its last act.
Before that happens, our three anti-heroes are living the high life despite being locked up, but there's trouble on the horizon when an old associate of Dodger's, one Soapy Stevens (Wilfrid Hyde-White) turns up at the jail in the guise of a vicar. He manages to arrange a meeting with Dodger and after smiling through his insults, outlines a new plan to relieve a Maharajah of his extensive diamond collection. To carry it off, he and his two cohorts must escape from prison, pull off the robbery of the security van, then break back into prison without the authorities knowing about it.
However, there are complications when their favourite warder, the avuncular Jenkins (George Woodbridge), announces he is going to retire which is unfortunate for the prisoners because his replacement is the notorious hardliner Officer "Sour" Crout (Lionel Jeffries, ideal). Crout is nothing less than horrified about the lax conditions at the establishment, and worse than that could recognise Soapy, so represents a double threat to the success of the crime. In the meantime, Dodger and company have to figure out a way to get free without jeopardising their actual release in a few days' time.
Among the incidental pleasures are some off colour jokes, such as the visiting day where one inmate asks how his wife can have an eight-month-old baby when he's been inside for two years ("But Fred," she replies, "You sent me such wonderful letters!). And the cast know everything expected of them so from the stars to the smaller character parts, there's no danger of being let down in that department even if Sellers acts as if Dodger is suffering from a permanent headache. If there's a flaw, it's that the big laughs of the first half dry up a little for the second, where pulling off the crime becomes paramount, but there are still chuckles to be enjoyed, and the way they liberate the diamonds is inspired. Can they get away with it? Well, that might be too much to ask, but it's fun to watch them try. Music by Ken Jones.