Springing onto the page in 1963, written by Stan Lee and pencilled by Steve Ditko and Sol Brodsky, Spider-Man has become one of Marvel's most popular heroes - and from then to now, he's grown from a hot-headed teenager into a legend among the superhero community.
These days, his character is renowned for three of his best qualities: his web-slinging, his quick wits, and his big heart.
While Spider-Man's heart and webs are never in question, there have been times when his wits have been put to the test - and even times when they've been found wanting.
A surprising number of the web-slinger's enemies have proven that they're not just able to out-punch him, but that they're able to out-think him, too - which almost always leads to disaster for our young hero.
Spider-Man's rogues gallery of evil scientists, criminal masterminds, and giggling madmen have come up with some shockingly complex schemes to get the upper hand on our favourite wall-crawler over his long career as New York's defender - and the entries on this list are some of the most dramatic and the most devious.
From anti-Spider gadgetry, to psychological warfare, to using his own powers against him, here are ten times Spider-Man's villains thoroughly outwitted him.
10. Tombstone Fights In A Phone Booth - The Amazing Spider-Man (2022) #3
Lonnie Lincoln, AKA Tombstone, is better known for brute force and intimidation tactics than his quick wits. However, over his many brawls with Spider-Man, Tombstone has slowly but surely figured out how to counter the web-slinger's fighting style.
Written in 2022 by Zeb Wells and pencilled by John Romita Jr., this comic sees Tombstone playing to his strengths with a calculated choice of terrain.
Spider-Man has gotten the better of Tombstone dozens of times despite the latter's impressive combat prowess - and this is due mostly to his pitched agility.
Though Tombstone is no slouch in a fistfight, with superhuman strength and unmatched durability, Spider-Man's massive speed advantage meant he spent most of their fights hitting air. Recently, however, he pulled a surprisingly cunning strategy. By luring Spider-Man into a cramped space between hydraulic walls - taking some of Spidey's best punches like a champ while he got into position - he robbed Spider-Man of any room to maneuver.
Catching the wall-crawler with a vicious body blow, he proceeded to crush his ribs in a bear hug, ending the fight. In just a few panels, Tombstone proved that as well as being strong, he's also more cunning than we realised.