Great thread! I'll have to follow some of the recommendations above! For myself, so far:
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Simon Baxter: not as many vids or as regular as some others, but his photography is fantastic, IMHO, and I love his attitude... & Meg!
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Thomas Heaton: often mentioned upthread, and always enjoyable, though maybe a bit less since he got a rail, not sure why...
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Thomas Shahan: very few vids, but a Pentax shooter and my favorite macro shooter.
Honorable mentions to Sean Tucker, Gavin Hoey and TCS TV.
I have to say it's quite humbling to see the work of these photographers/cinematographers who manage to not only shoot great photos, but also make enjoyable short films about the process of shooting great photos!
p.s.: if you like portraiture, you might also enjoy
this series of shorts on Arte (in French with English subtitles) by photographer Stéphane Lavoué about the story behind some of his famous people shots...