Is it my imagination, or did Joey from Friends get increasingly more dumb as the series progressed? He started out as a goofball but reliable friend who was prone to misunderstanding, but for the spinoff he was borderline institution material who couldn't hold a job.
Television
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Brooklyn 99 had a few examples but the most egregious in my opinion was Gina.
Michael Schur shows that are left open-ended tend to get very bad about this, though to be fair it's because they start so strong that the dropoff is more disappointing. The Office (US) and Parks & Rec both suffer from it in later seasons, and in my opinion P&R gets way too much of a pass for it. The Good Place was more tightly plotted, had various escape valves for weirdness, and ended before it got too far off the rails.
Maybe not the worst case of flanderisation, but Britta in Community comes to mind.
Jeff even lampshades it. "You seemed smarter when I met you."
Dunno if you'd want to count it as a TV series persay, but easily Usopp from One Piece. The man goes through an incredible arc of self-discovery before the timeskip, gets hyped as having finally conquered his fears, only to get reverted to his typical cowardice gag every post timeskip arc.
All of the Straw Hats suffer from flanderisation in post-timeskip One Piece, but IMO Usopp's is the worst, since it reverts him to a flat character that's heavily uninteresting.