Does this count?
(no poker though)
and they shoulda made a music video from this for I Wanna Be A Cowboy
Some other ones off the top of my head:
Billy Joel - Uptown Girl (w/ Christie Brinkley)
Fountains of Wayne - Stacy's Mom (w/ ex Mrs Rod Stewart, Rachel Hunter) (btw, Postmodern Jukebox has a fun cover)
Van Halen - Hot for Teacher (w/ Lillian Muller who was also in Rod Stewart's Do Ya Think I'm Sexy)
David Lee Roth - California Girls
ZZ Top - Legs
Dwight Yoakam - Suspicious Minds
Huey Lewis & The News - Happy To Be Stuck With You (w/ Mrs Pierce Brosnan, when she was thinner)
Luis Fonsi - Despacito (w/ Miss Universe 2006 Zuleyka Rivera)
Lee Brice - Woman Like You
Michael Buble - Save The Last Dance For Me
Shania Twain
Belinda Carlisle