Madeline Bassett is a recurring character in the Jeeves stories by English comic writer P. G. Wodehouse, being one of the young women to whom Bertie Wooster periodically finds himself threateningly engaged.
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Wooster describes her in Right Ho, Jeeves as " a pretty enough girl in a droopy, blonde, saucer-eyed way, but not the sort of breath-taker that takes the breath ", though elsewhere he describes her as "physically in the pin-up class". These moderate charms must be considered in balance with her personality, which is that of the soppiest, mushiest, sentimentalest young gawd-help-us that ever was; even the devotion of Gussie Fink-Nottle wanes with each new injunction to take up vegetarianism or recite Christopher Robin poems at the village concert.
To illustrate her unique outlook on early 20th century life, it may help to mention that Madeline is allegedly fond of remarking in casual conversation that "the stars are God's daisy chain", or that "every time a fairy blows its wee nose a baby is born". Such comments would be in keeping with her general conversational style, which is all too apt to revolve around elves, gnomes, flowers, and small furry creatures. This excessive soppiness is wedded to an impressive degree of self-centered idealism, which for nearly the entire course of the saga keeps her from being wedded to anyone else; at the end of Jeeves and the Tie that Binds she is re-engaged to Roderick Spode and may be presumed to be on her way to becoming the next Countess of Sidcup, as long as he does not make the error of relinquishing his title or speaking ill of Winnie the Pooh.
When not visiting some country house or other as the plots of the books demand, Madeline is generally to be found at Totleigh Towers where she lives with her father, ill-tempered magistrate and silver collector Sir Watkyn Bassett, and her father's ward Stiffy Byng. The two girls seem to be on good terms, Madeline supporting Stiffy's secret engagement to Stinker Pinker, but Stiffy has little trouble in perceiving Bertie's unwillingness to be leg-shackled to La Belle Bassett and makes extensive use of said unwillingness with blackmail.
This threatened matrimony comes about originally due to Madeline being a friend of Bertie's cousin Angela, the daughter of his Aunt Dahlia Travers. In Right Ho, Jeeves, they meet on a trip to Cannes during which she believes that he is gazing at her with long, dumb, searching looks. What for Bertie is mere terrified longing for his warm safe apartment and the comforting presence of Jeeves and a nice cocktail, Madeline mistakes for pining love; and when he pleads in the third person the cause of Gussie Fink-Nottle who adores Madeline from afar, Madeline of course mistakes his plea for a proposal from Bertie. She gently rejects his proposal, as she has been infatuated with Gussie since their first meeting; however she assures a relieved Wooster that, if ever she felt the need to return Fink-Nottle to the store, Bertie is the first person she'd look to as a replacement fiancé. The health of her various engagements forever thereafter hangs over Bertie's head as a sort of Sword of Damocles.
Madeline typically thinks that Bertie comes to where she is to display his pining, everlasting adoration, when he's actually either there for reasons having nothing to do with her, or to try to save her current relationship.
Through an unfortunate misunderstanding, Madeline comes to believe that Bertie is in love with her, but (fortunately for Bertie), she becomes engaged to his friend Gussie Fink-Nottle. When he elopes with Emerald Stoker, she renews her engagement with Bertie, before becoming affianced to Sir Roderick Spode, later 7th Earl of Sidcup.
In the ITV television series versions of the P.G. Wodehouse stories, Madeline almost marries Spode, but the attempted wedding is ruined by Tuppy Glossop's pipe clearing rust-bucket "Plumbo-Jumbo", in the series finale "The Ties That Bind".
In the third and fourth seasons of the ITV series Jeeves & Wooster, 1992–1993, Madeline Bassett was played by Elizabeth Morton, having been played in the first two series by Francesca Folan and Diana Blackburn respectively.