Radio Bleak Expectations: Three of the four protagonists begin here, main character Pip Bin, his sister Pippa, and Pip's best friend Harry Biscuit, of the Warwickshire Biscuits, to varying degrees of severity. Pip is an utterly oblivious twit, with the self-preservation ability of a dead dodo, easily fooled by the flimsiest of Paper Thin Disguises. Even the Creator of the Earth can only say he's "basically" good.
Pippa is an animal activist, but her idea of helping is massively off. Even worse is when Pip insists the family start performing charitable deeds. Pippa's initial contribution is to have luncheons with other women, rather than actually do something charitable.
Harry, meanwhile, is all twit, never on the same page as anyone else, but never malicious (except when he's turned evil). The problem is Harry wishes to be a famous inventor while being utterly terrible at it.
Giles Wemmbley-Hogg is not actually malicious, just incredibly naive. Most of his attempts to hold a job don't go well, but having wealthy parents means that he's able to go around the world, keeping an audio diary of his travels.
Theater Sir Evelyn Oakleigh in Anything Goes. (P. G. Wodehouse was one of the authors of this musical.)
In The Cradle Will Rock, Junior Mister and Sister Mister, the son and daughter of the rich Mr. Mister, lead lives of ease and boredom. To do something about Junior's obvious shiftlessness, he gets sent to Honolulu on a pseudo-journalistic sinecure.
Der Rosenkavalier has Leopold Anton, Baron Ochs (German for "ox") auf Lerchenau, the Marschallin's Country Cousin. He tends to assume that privilege will protect him from the consequences of his foolishness.
The entire D'Ysquith clan from A Gentleman's Guide to Love and Murder with the exceptions of Phoebe (who is implied to have figured out Monty's scheme by the end of the play and uses it to her advantage), Monty (who grew up a bastard of the family and thus had to work his way to the earldom with cleverness), and possibly Monty's mother (who was banished from the family upon marrying a Castilian and dies in poverty). Notably, the show is heavily influenced by Gilbert and Sullivan and music hall productions of Victorian and Edwardian England.Lord Adalbert D'Ysquith: I don't understand the poor. I don't understand the poor. The lives they lead of want and need, I should think it would be a bore! It seems to be nothing but stubbornness. So what's all the suffering for? To be so debased is in terrible taste, I don't understand the poor!