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This is something I've posted before, some people might (or might not) recognize it.
Dylan
Normal Gym leader
Relatively early in the game, 2nd or 3rd Gym
Pokemon would be Ambipom, Loudred (later Exploud), Chatot, and Audino
Signature Pokemon is Ambipom
Rising from the underground music world to be the star of the music trends across the region, Dylan plays a wide variety of music on his signature guitar and uses varying Pokemon to achieve unique sounds.
The gym itself would be a huge musical venue in the shady part of town, standing out amongst the gang tags and improvised skating rinks at night with its loud music and neon glow.
The gimmick of the gym would involve navigating a neon-colored maze full of psychadelic musical themes entirely by ear, and trainers along the way would battle you in a "mosh pit" kind of craze.
Dylan himself is a rather laid-back dude (almost obviously a stoner caricature), but his moods and music can change violently in the heat of battle which makes him rather unpredictable. Unlike most trainers, Dylan is more likely to use oddball strategies, and swaps Pokemon to fit type match-ups more coherently than most. His Chatot is a dark horse against most trainers thinking they have an easy sweep with a Fighthing-type Pokemon.
Upon defeat, Dylan mellows out and sends the fans packing as the venue dries up. he then becomes staunchly sober, gives a small speech about doing your damndest to rise up out of any situation like he did with music, and hands out the Note Badge and TM 49 (Echoed Voice).
Later on in different conditions, Dylan can be fought in a much more difficult re-match to get infinite copies of TMs like Belly Drum, Baton Pass, Encore, Heal Bell, etc. so long as the player does not use the same Pokemon against him more than once.
