Brody Jenner may have found himself in the middle of some priceless Hills situations -- epic exchanges with his on-again off-again pal Spencer Pratt, flirting with Lauren Conrad/Jen Bunney/Audrina Patridge/Kristin Cavallari (to rattle off a handful of lucky ladies) and having the distinction of being the final cast member to appear on the series in the Hollywood studio lot front of the Hollywood sign, to name just a few. But through it all -- the good times and the, well, dramatic -- the handsome, newly engaged SoCal stud was known for melting hearts while flashing that unbelievable smile.

In honor of the upcoming 10th anniversary of the hit program, we've compiled the best moments of the notorious ladies' man grinning and showing off those perfect pearly whites. From that first date with the lovable Teen Vogue intern (BOTH of their expressions!) to beaming while partying with his friends at Les Deux, there is absolutely no shortage of the unforgettable MTV alum smirking. WHAT A GUY.

Enjoy the mashup video of the beautiful Brody Jenner above, share your favorite memories of him in the comments and be sure to stay with MTV News for more coverage around this pop culture milestone!