Ever wondered what might happen if some of your favorite literary characters were to meet in, well, new fictions created as sort of parallel narratives? While there have been many parallel narratives and retellings of classic or well-known stories, we rarely find characters crossing over into different stories. Which would be a lot of fun, when you think about it. Happens more in certain kinds of movies, but not so much in books.

Here are some of my favorites, in no particular order. At some point, we’ll explore them in a lot more detail.

1) Mrs. Dalloway and Molly Bloom: It is well-known that Virginia Woolf had a sort of hate-jealousy relationship with James Joyce. Yet, both gave us such beautiful interior monologues for both of these characters that it would be fun to cast them in a story together. Just think: the genteel and refined ‘Mrs Dalloway‘ meeting the more earthy and slutty Molly Bloom from ‘Ulysses‘. The possibilities are too delicious.

2) Anna Karenina and Madame Bovary: Both tragic heroines had extra-marital affairs. One is Russian and the other French. And remember that high society in Russia during Karenina’s time spoke French mostly. Can you imagine these two meeting on a train somewhere and exchanging notes on how to cuckold husbands. Actually, they might also commiserate and sympathize with each other, don’t you think?

3) Portnoy and Hamlet: Yes, entirely different centuries and cultures, I know. Hear me out on the common themes that unite them somewhat. Firstly, both of them indulge in lengthy monologues. Secondly, both have a mother-fixation. And, thirdly, both have a deep sense of self-loathing. So, this is a match made in heaven, of course. I do think that Portnoy would tire more quickly of Hamlet than the other way around.

4) David Copperfield and Huck Finn: Twain and Dickens must meet through their characters, of  course. Why Copperfield and Finn? For one, both characters have these lifelong servant-friends: Peggotty and Jim, respectively. Then, there’s the whole issue of being passed from relative to relative while growing up. They would have some rather interesting notes to compare too.

5) Isabel Archer and Eustacia Vye: Henry James’ repressed heiress meeting up with Thomas Hardy’s wanton beauty. This is another case of opposites like #1. Imagine if Isabel had somehow run into Eustacia during her European travels and taken her as a lady companion. Eustacia, only too glad to get away from Egdon Heath, might well have, with her unconventional ways, influenced Isabel while getting to play the lady-of-the-world herself. Oh, I think they would have gotten up to some fun and Isabel might have loosened her stays a bit.

6) Holden Caulfield and Caddy Compson: OK, I debated this one internally quite a bit. But don’t you see how Caulfield could just fall for Caddy’s caring ways? Of course, she would completely change him. All that teenage angst and rebellion would turn into — what? — something else entirely. Yes, die-hard fans will balk. But, really, ask yourself: doesn’t Caulfield have to grow up sometime? Salinger and Faulkner would never have gotten on, of course.

7) Becky Sharp and Lolita: Another time-traveling connection here, but one based on similar character traits. Chiefly, that of using their charms to seduce older men. Becky was a social climber and Lolita and her mother had social aspirations too. Both became the most popular creations of their male authors: Thackeray and Nabokov. I’m sure that the latter, as a professor and critic, had something to say about Thackeray’s work at some point. In ‘13 Ways of Looking at the Novel‘, Jane Smiley made this connection:

Philosophically, Lolita is in the tradition of conservative novels by novelists who accept the innate evil of human nature, such as Thackeray. In conservative novels such as Vanity Fair, The Picture of Dorian Gray, and Lolita, redemption is as impossible to achieve as true connection, and the protagonist either remains isolated at the end or achieves a new degree of isolation as a result of the action of the novel.

8) Caliban and Falstaff: Shakespeare sometimes repeated minor characters across his plays, but these two have never met. Caliban, the deformed, monstrous son of a witch in ‘The Tempest‘ and Falstaff, the fat, vain, and cowardly knight who appeared in three plays. Now, imagine how much trouble these two could get up to together. Both have given memorable monologues in their respective plays, so, clearly, they could hold an entire play together as lead characters.

9) Dorothea Brooke and Hester Prynne: Oh yes, another British and American meeting up. A genteel lady from George Eliot’s ‘Middlemarch‘ and a defiant country-woman from Nathaniel Hawthorne’s ‘A Scarlet Letter‘. One was, again, sexually-repressed, while the other was sexually-liberated (well, as much as was possible in those times.) Both were flawed and complex and continue to be among the finest female characters in literature. And both were denied happy endings. If they met just when Dorothea disses her dead husband’s will and marries the man she loves (only to find that she is still subordinate to the male ego), don’t you think Hester would have a few quiet words with her about that?

10) Lily Bart and Lily Briscoe: Wharton and Woolf. The latter disliked the former’s work, considering her the old guard (there’s more in Woolf’s critical writings if you prefer to delve further into this). But, these two heroines from ‘The House of Mirth‘ and ‘To the Lighthouse‘, respectively, do have some common ground. Lily Bart was a social climber who, ultimately, wanted love and respect and, unable to reconcile these conflicting goals, had a sad end. Lily Briscoe was, similar to her namesake, a single, young woman visiting with people of a higher social station. While Briscoe’s doubts and internal agonies were more to do with women succeeding at independent talents and careers like painting and writing rather than making a good marriage, in the end, both women wanted the same things: respect and love.

So there you go. That’s my list. Do you have any similar fictional meetings on your literary wish list? Do share.

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