Seagram's 7

Playboy Nov. 1968

Old Crow Bourbon

Playboy Nov. 1968

Paul Jones

Playboy Nov. 1968

Seagram's 7

Playboy Sept. 1966

Two-fer Thursday: Winthrop and Old Hickory

Playboy Sept. 1964

Imperial Whiskey

Playboy Nov. 1967

Old Crow Traveler

Playboy Nov. 1967

Old Hickory and Sweaters

Playboy Nov. 1967

Summer Whiskey - Seagram's 7

Playboy July 1968

King George IV Scotch

Playboy Jan. 1969

I.W. Harper Bourbon

Playboy Nov. 1967

Seagram's 7 Crown

Playboy Nov. 1967

Dewar's White Label

Playboy Jan. 1969

J&B Scotch

Playboy Oct. 1968

Cutty Sark

Playboy Nov. 1967

White Horse Scotch

Playboy Nov. 1967

     Most of the ads I see that feature/include/show women do so in a less-than-flattering manner.  Probably due to the target audience of a Playboy magazine, but most of the time women are shown as being subservient and/or objectified creatures best suited to cater to man's pleasures, which of course makes such advertisements good targets for us modern-day readers to scoff and snort derisively at.  So I find this ad refreshing, as it features a jaunty pants-wearing woman who evidently plays and works just like the boys do.
     And let us not forget the awesome plaid/turtleneck/orange glasses combo.  Retch.

Johnnie Walker Red

Playboy Jan. 1969

Cutty Sark

Playboy Oct. 1968

Actually a pretty nice-looking ad.  Classy boat painting, at least.

Paul Jones Whiskey

Playboy Jan. 1969

     Ad text:   P.J. will take on all other whiskeys - without water, soda, or mixers to disguise the taste.  That's because Paul Jones is rich and different.  With flavor that speaks right up.  And smoothness that goes down right.  Get acquainted.

Fleischmann's Whiskey

Playboy Sept. 1964

Pretty sure you can't buy distilled liquors in that size.