Sean Connery

One of Sean Connery's earliest MAD appearances came in the inventive Mort Drucker-Frank Jacobs classic "007: The Musical." Originally appearing in MAD #94 (April '65)

Mort Drucker would get a few more cracks at caricaturing Sean Connery during his MAD tenure, most famously in "8 'James Bomb' Bomb Movies." The Arnie Kogen-penned round-up of the 007 franchise's first eight flicks, beginning with "Dr. No-No" (seen here), originally ran in MAD #165 (March '74)

Sean Connery won the Oscar for Best Supporting Actor following his portrayal as grizzled cop Jimmy Malone in the 1987 film update of The Untouchables. Here he is with co-star Kevin "Elliot Nice" Costner in one of my favourite MAD movie parodies of the late '80s, "The Unwatchables," written by Arnie Kogen and illustrated by Angelo Torres for MAD #276 (January '88).

Sean Connery as Dr. Jones, Senior in the MAD movie parody "Inbanana Jones and His Last Crude Days" written by Dick DeBartolo and illustrated by Mort Drucker for MAD #291

Sean Connery in MAD's parody of "The Hunt For Red October" called "The Hunt For Last October", written by Stan Hart and illustrated by Angelo Torres for MAD #297

Sean Connery in the MAD article "James Bond Villains' Pet Peeves" written by Desmond Devlin and illustrated by Drew Friedman for MAD #365

Tom Richmond, who has included every single James Bond actor within one of his limited-edition multi-character caricature prints, got to include all six Bonds - including Daniel Craig and Sean Connery, in this particular panel - in the art for the inventive Desmond Devlin-penned 007 movie mash-up "Casebook Spyfail: The Battle of the Bonds." Originally running in MAD #521 (June '13).