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What show took you the longest to get into?
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For me it's "The Mighty Boosh": https://youtu.be/FiU-oCWPhx0
I fell in love with my now ex-wife (then girlfriend) in no small part because she had great humor and I liked a lot of the shows she liked.
So when one day in 2010 she raved about "The Mighty Boosh", of which she owned all DVDs including the live stuff, I had to check it out.
I started watching S01E01 and felt like watching someone's fever dream trying to recreate a kid's show. Same for the second, third etc episode.
Usually I'd have long given up on that show. But there had to be something to it, if she loved the show so much.
So I started watching season 2 ("Milky Joe" or "The Priest and The Beast", I can't really remember) and it clicked immediately. From there I binged all other episodes + season 3 + season 1 again - and I loved it all and couldn't understand how I didn't like it initially.
And thanks to that I discovered other gems from the same "circle" like "Snuff Box", "Garth Marenghi's Dark Place", "Luxury Comedy" and "The IT Crowd" (some episodes haven't aged well, but others are just filled with gold).