Lisa Ann (GIFs) Through the Years

It’s been an incredible career for the inimitable Lisa Ann, who started out before the internet caught on, became famous in the era prior to tube sites, and who can still make a legitimate claim to be one of the most popular stars on the planet. In this compilation of Lisa Ann GIFs, we take you through her career year by year, spotlighting a movie and GIF from her earliest days right up to her comeback movie.

Tits A Wonderful Life

Along with Flesh For Fantasy, this is the oldest Lisa Ann movie still carried by Adult Empire on VOD. Trivia: Lisa’s scene partner in this early movie from her career is none other than the famous Vince Vouyer, later to found a studio of his own. (Is it just us or does Vince look oddly like Lisa herself at this angle and with his hair grown out?)

Dirty Western 2

Dirty Western 2 was another early shoot for Cal Vista, with whom Ann was under contract during the early years of her career.

The Wicked Web

The Wicked Web incorporates an early, now amusingly outdated internet theme into its plot. The tagline is “Get online with Lisa Ann.” Indeed!

Desperate House MILFs

Lisa took an extended hiatus from porn starting in the late ’90s, working as an exotic dancer and spa owner for several years, only to launch the first of two spectacular comebacks in 2006. Desperate House MILFs was one of her initial performances after her return.

POV Centerfolds 4

Viewers were able to get up close and personal with Lisa in this fourth installment of Zero Tolerance’s POV series.

Who’s Nailin’ Paylin?

Ann rocketed to mainstream fame when she took on the role of the much-lampooned VP candidate Sarah Palin.

Obama Is Nailin’ Paylin

Lisa followed her signature role with several sequels, including this 2009 effort that incorporated scenes with a Barack Obama lookalike.

Dirty Rotten Mother Fuckers 4

Flamboyance has always been a part of Lisa Ann’s style, as evidenced by this striking moment where she flings her head back in ecstasy.

Super Anal Cougars Part One

Lisa Ann helped bring the concepts of MILFs and cougars into the public eye in various “older woman”-themed movies, including this 2011 fave from West Coast Productions.

It’s A Mommy Thing 6

2012 was another election year, but by this point, Lisa Ann had left political spoofs behind, focusing instead on her identity as the world’s most famous MILF.

Big Tit Centerfolds

The latter portion of Lisa Ann’s second career phase saw her appear in many high-key, glamorous porn movies, including this elegantly photographed effort from Kevin Moore.

MILFs Go Black For More

Not long after this scene was released, Lisa announced her retirement from porn, deciding to focus instead on a career in fantasy sports.

Lisa Ann: Back 4 More

For a time, it seemed the world of porn had seen the last of Lisa Ann, but she made a triumphant return to the industry in 2018 with Lisa Ann: Back 4 More (pictured here in the movie’s final scene, featuring Isiah Maxwell).

Browse Lisa Ann porn movies here.