Cracked and its various specials and spinoffs often repackaged materials so much and I've posted excerpts on this blog so randomly it's hard to tell what's been shown and what hasn't, but I'll try.
This is all from the second issue dated May 1958.
Most of their early covers, like this one by John Severin, had cavalcade covers, which had several things going on at once, and usually showcased who was famous at the time, probably inspired by Jack Davis' cover for Mad #27. It would take forever to identify everyone featured, so I won't. In addition to Sylvester P. Smythe, who was initially there to fix the cracks throughout the magazine (Cracked. You get it?), the other mascot was supposed to be the Veronica Lake look-a-like in the lower left. She's mentioned in the (fictitious) letters page I'll show next week.
Old Grand-Dad whiskey ads drawn by Paul Reinman.
Bill Ward which was used in the facsimile of Cracked #1 that I previously posted a couple years ago.
This looks like it was drawn by Russ Heath.
Kurt Schaffenberger I posted here.
Next was this magazine parody from Paul Reinman.
parody of Bridge on the River Kwai I put here years ago.
Then the Shut-Ups by Bill Ward I previously posted here.
parody of American Bandstand. More from this issue next week.