Back in December 2010, when we decided to launch vintage watches on Gilt Man, there was only one person to call: our friend Ben Clymer, who as founder and editor of HODINKEE.com, who has helped turn on a generation of guys to the appeal of a timeless timepiece. We’ve since run several curated sales with Ben, and for our latest we asked Mr. C to put together what amounts to a greatest hits collection of collectible watches. Highlights include a early-’60s Speedmaster; a Ref. 1016 Explorer; a late-’60s, meters-first Sub; a ’70s-era GMT Ref. 1675 with a Pepsi bezel; a killer Tudor military sub; and a gorgeous Jaeger Le Coultre Memovox. And because all that talk of references and bezels can get pretty geeky pretty fast, our Tyler Thoreson sat down with Mr. Clymer to learn more about what makes each of these watches so covetable and cool. Watch the video below, and shop the sale on Gilt Man Saturday, December 21, at noon ET.