I just remembered another interesting series: The Desert Peach by Donna Barr. It was a comic book series back in the nineties about Manfred Rommel, Erwin Rommel’s flamboyantly gay younger brother who commanded a support unit in the North Africa campaign.
I came here to mention Ciaphas Cain, Hero of the Imperium! Then I found out someone already had.
There’s The Walled Orchard and Goatsong by Tom Holt, which are set in Athens at the time of the Pelopennesian War; the protagonist is not quite Flashman-level awful but is definitely not heroic and very cynical. There’s a later book by Holt called Olympiad (I think) that is similarly cynical about ancient Greece. All three are quite different in tone from Holt’s usual light fantasy stories.
This is getting further from the OP, but Shakespeare’s Troilus and Cressida is a brutal deconstruction of literary conceits about the romance and chivalry of war. It’s bleak, bitter and cynical, and Homer’s culture heroes are depicted as knaves, fools, thugs , pimps and cynics, with the slave Thersites providing a mordant commentary throughout. It’s an astonishingly modern play for 1603; it reads more like it was written in Weimar Germany.
*The Red Baron Lives ! * by Brian Innes may be a candidate . In it the Baron survives his shooting down , but officially is declared dead. The British Secret Service blackmail him (I think) and recruit him to perform special missions for them as a pilot . He is still in hospital when the first seduction scene occurs and several follow. He is not portrayed as a coward but somewhat amoral. The mission described is an attempt to save the Russian imperial family before their execution. On the way he encounters Lawrence of Arabia, amongst other historical characters
It seemed to me that the book was laying a pathway for further adventures in the turbulent inter war years, but I am not aware of any sequels .
Looking up goodreads .com I find there is a book called *Red Red Baron * suggesting further adventures of the Red Baron in Soviet Russia .
In addition to my previous post I must add that the Baron was flying a large passenger cargo plane, the make which I cannot remember .
Banana Republican, by Eric Rauchway borrows the character of “sexist, racist, elitist” Tom Buchanan from The Great Gatsby and places him in the middle of the actual revolution/ American intervention in 1924 Nicaragua
They’re all pretty good as well, i’d recommend them.
Yes, Holt’s historical novels are good.
Another that comes to mind is Julian Rathbone’s A Very English Agent, which focuses, more or less, on the Peterloo massacre, with another bit about Shelley’s death in Italy. The protagonist is cynical and shifty, but otherwise quite different than Harry Flashman: unimposing, obscure, and poor. Looks like Rathbone wrote several other historical novels. I should look into them.
I’ve read a couple of Rathbone’s historical novels – reckoned them rather weird, but fascinating. One was The Last English King, which I gather is his most acclaimed novel: the first-person narrator being a member of King Harold’s house-guards at Hastings. A trait of this book, is the author’s jest of slyly slipping in various anachronisms – which I enjoyed, but which could imaginably grate on some readers. Have also read his Kings of Albion – a mission to England during the Wars of the Roses, undertaken by a small group of dignitaries from a state in India, who are considerably more civilised and knowledgeable than their English counterparts.
I found what I’ve read of his Very English Agent books OK, but was not immensely taken with them – just a matter of personal taste, no doubt.