I like the 3rd ones with the polished lip. Here are some American Racing "New Release" wheels from TireRack.com look pretty race style and masculine to me.
2002 Chevrolet Monte Carlo SS

 

prob is I cant decide and its a $1k choice. wheels and tires. I like the 5 spoke and the mutli spoke 5-10 designs mag and reg spoke. some of the ones I looked at i see on other montes so i backed off of those. Looking for some recommendations with links if possible. I have like 10 wheels bookmarked and changing them with input. It will have a body kit that looks more nascar then ricer. all i know is from input gloss black with machined lip which is how I was leaning befor. size i was thinking 18s but seen 20s that look cool too.

 

I'd go with the 3rd set

 

I like the the Cragers too. they are classic.

 

Everyone agrees with gloss black but split on mag style or spoke so I think I am going with something like this.

 

the last one in 20s....nice looking rim...i likey!!!!!!

 

Blacks rims on a black car just looks bad in my opinion

 

I like em i think they would look great

 

What he said ^^^^

 

X3 I'd do 18's though... Definitely not 20s if your going for a racer look? Some 20's are starting to grow on me though so idk but I do agree on something different than you've seen on other Montes.