r / June 21, 2011 1:19 AM

There's many things to list, but what comes to mind for me (in my own little world) is:

Smartest: Stick immersion blender. That thing does wonders.

Not so Smart: Cookies, every time.

Andrew / June 21, 2011 1:30 AM

Wisest? That's a tough one. Maybe our Prius -- when I commuted out the suburbs for work, it meant filling up once a week instead of twice or thrice, and even now we get over 40MPG in the city.

Dumbest? Probably buying a dual tape deck component for my stereo system. About a year later iTunes came out and made burning mix CDs so easy I probably only used the tape deck once. (Still have it though; happy to sell it cheap if anyone's interested!)

Mike / June 21, 2011 10:53 AM

Wise - Wedding ring

Not wise - that damn candy bar I just ate.

Mucky Fingers / June 21, 2011 11:47 AM

Wisest purchase - every Schwinn bicycle I've had since youth.

Least wise purchase - the one time I didn't buy a Schwinn.

Cinnamon / June 22, 2011 3:10 AM

Wisest: probably our condo, which we sold just before people stopped buying condos in Rogers Park

Worst: Never, ever buy a used car from someone who owns a junkyard. And if you do, don't drive it cross-country by yourself.

Charles / June 22, 2011 10:42 AM

Wisest - I bought my sister an awesome hanging lamp for her dining room. This one purchase may have made up for years of dealing with me as an older brother.

Least wise - My first pack of cigarettes.

maardvark / June 23, 2011 3:06 PM

Wisest: A GPS for my directionally-challenged brother. Now we no longer have to spend hours waiting for him while he gets himself un-lost.

Least wise: Every beer after the third, on any given night. (Yet it keeps happening!)

maardvark / June 23, 2011 3:08 PM

"Wise - Wedding ring"

Even wiser: saying that where your spouse can hear it.

eee / June 24, 2011 12:40 PM

Wisest: that eHarmony 3-month subscription. Without it, I never would have met my spouse.

Worst: possibly the elliptical machine I rarely (if ever) used. What a dust-catcher.

Ron / June 26, 2011 8:01 PM

Wisest - A few thousand original prints by a now famous photographer.... for two hundred fifty bucks.

Worst - sushi that landed me in the hospital for a week.