If you loved how Gravity's Rainbow weaves together the stories of Tyrone Slothrop, Roger Mexico, Katje, and dozens of others across continents and decades, you'll be captivated by 2666. Bolaño's masterpiece plunges you into the intersecting lives of critics, journalists, professors, and criminals, all orbiting the enigmatic figure of the author Archimboldi and the unsolved murders in Santa Teresa. The ensemble cast is dazzling, and each narrative thread is both richly detailed and hauntingly interconnected.

If the intricate, time-jumping structure of Gravity's Rainbow drew you in, The Recognitions will feel like a revelation. Gaddis crafts a wild, shifting narrative—moving between art forgeries, religious symbolism, and bohemian New York—that refuses to follow a straight line. Like Pynchon, Gaddis expects you to piece together the story from scattered clues, unreliable narrators, and thematic echoes, rewarding your close attention with layers of meaning.

If you found yourself laughing at the absurdities and dark wit sprinkled throughout Gravity's Rainbow—from Slothrop's slapstick escapes to the surreal bureaucracy of the White Visitation—then Catch-22 is essential. Heller's satire of World War II military life is packed with hilarious, tragicomic vignettes and unforgettable characters like Yossarian, whose desperate attempts to survive the system echo Pynchon's own brand of humor.

If the philosophical undercurrents in Gravity's Rainbow—questions about fate, paranoia, and the nature of history—resonated with you, The Man in the High Castle offers a similarly rich tapestry of ideas. Dick's alternative history plunges you into a world where the Axis powers won WWII, but it soon becomes clear that the true story is about the nature of reality and the stories we tell ourselves. The book's meditations on authenticity, destiny, and resistance are as thought-provoking as Pynchon’s.

If you were fascinated by the intricate conspiracies and overlapping storylines of Gravity's Rainbow, The Crying of Lot 49 is a shorter but equally enigmatic journey. Follow Oedipa Maas as she unravels the mysterious Trystero system, encountering cryptic clues, secret societies, and endless layers of meaning. Every detail could be a key—or another dead end—making for a brain-twisting, rewarding read.