Which One of Spider-Man's Enemies Could Give Batman a Nightmarish Existence?

[Minerboh]

Same as at Spidey's senction, which one of Spider-Man's enemies could destroy Bruce's life?

[Carabas]

Does Mephisto count?

[MajorHoy]

Did Tom King ever write Spider-Man?
If not, it's still hard to top him for screwing up Bruce/Batman.

[oasis1313]

Sand Man could flood the Batcave with sand.

[Hilden B. Lade]

Catwoman catches Batman and Black Cat exchanging a few more than friendly passes at each other. Now whenever Bruce puts the Batsuit on, or gets in the Batmobile, they distinctly smell like someone snuck into the Batcave and smeared kitty litter all over and inside them.

(Is Black Cat still a villain atm? I haven't kept up with the Spidey books)

[WonderScott]

I think of Black Cat as more of an anti-hero or full on hero.

I'd go with Kraven or Kingpin.

I like the idea of Bruce Wayne and Wilson Fisk doing battle in the business and society circles of Gotham and Batman and Kingpin conflicting with one another on the shady side of Gotham.

[Restingvoice]

Norman Osborn, I guess, coz it's like having The Joker combined with Lex Luthor.

Also, Two-Face with the whole split personality thing if we go by the movie

[Celgress]

Sandman, Electro, Venom, would all be a physical challenge due to their different abilities.

Osborn, if he learns Batman's secret identity, would be hell to deal with as he is in many ways a cross between Joker and Luthor.

[Shriveling_memo]

Sandman, Electro, Venom, would all be a physical challenge due to their different abilities.

Osborn, if he learns Batman's secret identity, would be hell to deal with as he is in many ways a cross between Joker and Luthor.

Batman should not be allowed to beat super strong villains. Osborne should rip him in half. King pin, hobgoblin, sandman as he's like clayface to a point.

[Derek Metaltron]

Norman Osborn, because he is as much a danger to Bruce Wayne as he would be as Batman. OSCORP and Wayne Industries would constantly be at odds with each other (and probably Lexcorp too).

Ock could be interesting since he'd have the science prowess of Freeze but the arrogant intellect of Hugo Strange or Riddler. Though he'd likely need to keep adapting his tentacles to keep up with Bruce's anti-Ock technology.

Kingpin would be Penguin mixed with close to default Bane level strength, and a dangerous opponent.

[Aioros22]

The usual suspects: Norman Osborn, The Jackal, Octopus (especially from last decade) Kingpin and the symbionte.

[Frontier]

I think Doc Ock would be an interesting challenge for Batman since he's both intellectually dangerous and physically dangerous.

Batman should not be allowed to beat super strong villains. Osborne should rip him in half. King pin, hobgoblin, sandman as he's like clayface to a point.

Once he learns Venom's weakness to sound he would probably whip up something that would give him an instant edge.

[K7P5V]

Kevin Smith's Mysterio

[Carabas]

Kevin Smith's Mysterio

Hasn't Kevin Bloody Smith done enough damage to Batman?