41% stings!!!

Yep. That's what's being taken out of my commissions four times a year. 41%.

I'm minimizing the impact by jacking my 401(k) up, but is there a way I can have a higher amount taken out of my supplemtal income (bonuses and commission) while not affecting my regular pay?

Secondly, does anyone have any tips to keep Uncle Sam out of my shit as much as humanly possible? Other than IRAs/401(k) and other traditional tax shelters?

Its well worth the effort to spend some time learning about taxes, at the very least hire a good accountant. Personally, I claim 4 throughout the year and I'm single with no dependants. While many may not agree with how Charles Givens went about his business, his "More wealth without risk" opened my eyes to tax issues.

uncle sam taxes the fuck out of commissions.

Isn't just withholding?

When you file in April, you should get a portion of that back. Or at least your should, if you have done a little planning.