https://osu.ppy.sh/b/2667 Ootsuki Kenji - Hitotoshite Jiku Ga Bureteiru [Insane!!] took me about 300 tries to pass, and was one of the first Insanes I passed.
https://osu.ppy.sh/b/53380 IOSYS - Border of Death [Lunatic] took me about 180 tries to pass (and a huge amount of time since most fails were in the last 20 seconds and the map is about 4 minutes long).
https://osu.ppy.sh/b/133476 Skrillex - Bangarang (feat. Sirah) (Cut Ver.) [LC] took me about 300 tries, but most of them were in the first 30 seconds.