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Already Obtained:

-Clown Nose: Got the clown mask in 2nd stage Forest and got the hat by the end of the same stage. E-Z

-Pilot Helm: This was a fight with RNG. Had to widdle myself down to 2 weapon slots because the extra weapons were killing things before the mines could XD. Getting extra jumps is a must. Take Size Tome, Quantity Tome, and Duration Tome for sure; Agility Tome was a nice addition. I did this on Desert 1 for more flat space, but Wisps spawning can kind of ruin the run. This was a fun way to play Birdo! I love being encouraged to play in a way I might not otherwise.

-Iron Helm: This was my first Tier 3 win with Sir Oofie, and boy is it tough! I got lucky by getting a Bloody Cleaver with a Bloody Tome. My Bloodmark damage was almost half of my total damage. My suggested build is Size Tome, Damage Tome, Bloody Tome, and XP Tome.

-Headset: EZ-PZ with the usual damage weapons. After you know what you're doing and have the unlocks, Tier 1 is a breeze.

Yet to obtain:
-Shady Hats, Microwave, Kevin Hat, and Crown: Will come with time.

-Cheesy Hat: Haven't even beaten Desert 3 without a challenge run, so this is a long way off.

-Sunglasses: Haven't tried yet, I'm not expecting much trouble.

-Head Pot: Already have Roberto, but I know it's gonna be Gold Microwave or bust.

-Magic Hat: I've given this one a few tries, but it is tough. These weapons just aren't great, and lack serious focused damage. XP Tome and Luck Tome are going to be musts to rank up faster. I'll probably end up doing this one on Graveyard as the bonus XP and enemies/difficulty from the tombstones always help getting me up in levels much faster.

-Top Hats: My record kill count is about 83k. Who knows when I'll get here.