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Frank Castle's crew...

Inspector 'Dirty' Harry Callahan, SFPD
Lt. Frank Bullitt, SFPD
Lt. John McClane, NYPD
Jack Walsh, bounty hunter and former Chicago police officer
Lt. Columbo, ??PD


Kingpin's crew...

Marsellus Wallace
Jules Winnfield
Vincent Vega
Vic Vega aka 'Mr. Blonde'
Keyser Soze aka 'Verbal Kint'



None of them have past experience or knowledge of the other.

Fight takes place in a Gotham-like city.

Only way out is Death or Incarceration.

I think the H2H match ups initially would look like this...

Punisher vs Kingpin
http://images.wikia.com/deadpool/images/f/fb/Punisher_says_smile.pnghttp://www.the-isb.com/images/Kingpin.jpg

Dirty Harry vs Jules Winnfield
http://nachrichtenbrief.files.wordpress.com/2010/05/eastpunk2.jpghttp://cliptank.com/PeopleofInfluencePainting_files/dude.jpg

Frank Bullitt vs Marcellus Wallace
http://3.bp.blogspot.com/_0Htwpiqateo/Sc4PjpLAkiI/AAAAAAAACEI/H4VHIBGxcPk/s400/bullitt_xl_01--film-A.jpghttp://images-mix.netdna-ssl.com/w/318/h/318/q/90/upload/images/extaudio/9f41defe-5eaa-49c4-ad1b-fd2a813b092c.jpg

John McClane vs Vic Vega
http://www.grudge-match.com/Images/diehard.gifhttp://www.rasmenia.com/wp-content/vic-vega.jpg

Jack Walsh vs Vincent Vega
http://www.imfdb.org/images/thumb/2/28/Mrun-cds2.jpg/500px-Mrun-cds2.jpghttp://www.quotesworthrepeating.com/wp-content/uploads/2012/01/Vincent-Vega.jpg

Columbo vs Verbal Kint
http://4.bp.blogspot.com/-SFomAiN4dl0/TgYFwohxpZI/AAAAAAAAC58/ymrYMyOMyB4/s1600/Peter-Falk-as-Columbo2.jpghttp://happyhourvalley.files.wordpress.com/2007/12/verbal-kint.gif


Discuss....

Have to say, I'm disappointed this thread hasn't gotten one reply in over 10 years.

Because at the end of the day it all comes down to kingpin and The punisher. All these movie characters are complete fodder to comic street levelers. either one of them could casually solo both teams and wouldn't even be slightly winded.