an only slightly illegal and not dangerous or creepy way for teen to make money?

You could have him sell pirated software.

Selling clothes ripped off from the salvation army. Or maybe reselling designer clothes at full price when he got them from the cast off bin?

Regardless, selling stolen jeans has been tested, tried, and proven a great money maker.

I would stear clear of the drugs issue as that is really a DEA federal crime that is more 'streets' type stuff. The selling of papers would be good, he could read and write papers to put up on a clearinghouse website, since he is smart.

Denise Gardinier
"Being an author is like being in charge of your own personal insane asylum." -G Harmon

16? He should be old enough to start bagging groceries at that age...
Suburb kids sell their pain meds like crazy where I'm from, but not to college students. It's more like ripping off freshmen, charging $10-15 per pill. Or, slightly milder, they get their 18 and older friends to buy them cigarettes to sell.
If you want to stay away from drugs, you could have him pirate DVDs or something.

Selling papers? ( I mean the kind that you have to write for school)

I don't think a fun teen novel should model a behavior that can get you thrown in federal prison and/or significantly fined (pirating/drugs), but maybe that's just me.

How about hiring himself out as a teenaged private detective, ala Veronica Mars? He could spy on kids for their significant others who think they're cheating. Not exactly illegal but not "nice" either.

Or, he could charge other kids to be their alibis when they want to be somewhere their parents don't want them to be. That could be amusing. Like, he'd have a list of names of people who are supposedly with him but always mysteriously unreachable when their parents call to check up. Or, maybe he's done some theater and can imitate their voices. Maybe you could have him really screw it up at some point.

Or, like someone else suggested, just have him get a job at a pizza parlor or as a dog walker or something. Maybe he could start his own enterprise house sitting for people who are out of town and not tell his parents, which could lead to all sorts of wacky misunderstandings (someone thinks he's a burglar/he witnesses a crime/finds something he shouldn't have seen in the house).

I was thinking the same thing :) If your story is lighter, maybe you could have him find funny ways to avoid telling his parents, etc, that he's gone the illegal internet route for money. Pirated music, too, would be neat...maybe he could run into interesting tunes that could give him clues if you stick with a mystery.

Story sounds cool, though!

Maybe he could do something like the red paper clip guy did? http://oneredpaperclip.blogspot.com/

If it's a fun mystery type story, then maybe he falls into it accidentally, like he finds a little girls kitten for her, and the parents pay him. So he goes to the park looking for someone else who's lost a pet. Maybe he pulls signs off of telephone poles for lost pets.

Hi everyone -

Thanks, I am totally inspired! These are really insightful comments and everyone got the idea of the tone right. Love the lost pet idea - it's enterprising, sweet and fits the detective genre.

You guys are awesome. Thanks for taking the time out from your writing to write me. I'll give full credit when this thing gets to the finish line!

-devonshire

" 'Only one man may hear my secret and live, and I would not wish to be responsible for your death.' "

--Salman Rushdie, The Enchantress of Florence

My brother had a friend who used to burn CDs and sell them at school. Mind you, this was around 2003, and a lot of our classmates didn't have CD burners so whoever had one and had a fast connection could make a nice bit of money selling bootleg copies. Or he could always sell pirated movies.

There is nothing impossible to him who will try.--Alexander the Great

You say he's smart: have him sell essays to the other kids at school. Fifty or One Hundred bucks a paper adds up pretty fast.