Aunt Petunia has died without leaving a will and the best way to stop Chuckle Manor from being bought by greedy Simon Chortle is to find the second of a matching pair of priceless drinking jugs - which involves time travel, so that the brothers demolish Stonehenge, watch Beethoven compose his fifth and have a run-in with a scary Tudor headsman, who comes back to the present with them.
Paul and Barry get involved in ice cream wars when Giovanni Slackoni sets up in competition to Chuckle Ices by buying their cornets cheap and selling them at a profit. Paul brings in his own ice-cream maker - a cow - but Barry saves the day by exposing the council official who has been hounding them as the brother of the non-Italian Giovanni.
Paul sets up a fans' convention weekend for the comic super-hero Beetleman, but the Beetleman who actually turns up is not the same one that everybody is expecting. Barry, however, is in a position to save the day financially when it turns out that he possesses the extremely rare and valuable first ever copy of the Beetleman comic.
Barry is in possession of the winning lottery ticket which will scoop the brothers fifty thousand pounds provided it is presented within two hours. He thinks he left the ticket in a recently-returned library book but now someone else has borrowed it and he's moving house so the brothers pose as removal men, causing so much damage there is precious little prize money left.
The Chuckle Brothers go to visit their grand-dads in a retirement home but can't find them. Instead they stumble upon a racket whereby the greedy matron is forcing the residents to prepare and pack in-flight meals for Fly-by-Night airlines. When they locate their grandfathers they all combine with a put-upon nurse to stop the matron's little game.
Paul and Barry are employed as care-takers at the Tower of London, ensuring that the ravens are safe and are not going to leave. They run into Daring Derek, a notorious thief out to steal the Crown Jewels ,and of course they scupper his foul plans.
Christmas Eve 1929:- On their way to Granny Chuckle's charades party the Chuckle Brothers are stranded at Little-Under-Standing and end up at Halle Bere Hall, once owned by Paul's friend Julian, but now occupied by his nephew Ralf. There is a jewel thief known as the White Glove on the loose and the brothers pose as female musicians to stake out Chives the butler, whom they believe to the burglar. However he is an undercover detective who joins forces with them to expose the real White glove.