I want to assist a few makeup artist because I know I still have so much to learn business and technique wise. How should I approach asking to assist?

I'd say first be Very aware of the artist you want to assist body of work and clients as you will potentially be working on those jobs and clients

Know the artists work

Now for when you approach them ..... 

Try to form some sort of bond , friendship , communication with them prior than just asking ," I love your work and I'd love to assist you "
At least 80 % of being hired by an artist is because we enjoy your company , we don't really know you or trust you yet even if you are  a "kick Ass" artist were going to be spending alot if time on set

You have to remember you represent us and our "brand" and whatever happens on set with you will solely reflect on us , so try to know them, form a bond , comisirate ........  Build trust

I can't  tell you how many people have emailed me to assist and I have no idea who they are lol  , why I should bring them in ,  I just get the same. " hi. I love  your work , I know I can learn alot from you and I'd love To assist you ...     " insert random names " lol

You got to do better than that

You also have to realize we all already have a pool of artists we work with who assist us and we assist them .... We pass jobs to each other  So when you ask to assist your also potentially taking away an already trusted colleagues work or a friends .... And someone who may throw us back work

So don't be offended if your cold , unconnected request either gets ignored or the ole.  "Thanks I have your information , ill let you know if I can use you ",,,   remember if you haven't formed any sort of rapport your just another blank invisible artist wanting to assist ....   

Most of us hire people we like to spend time with 

Hope that helps

Trial and error.  I email alot of people and only hear back from very few.  Surprisingly, I hear back from the 'bigger' names more than I do from people that are closer to my level.  Artists tend to be pretty protective of their territory.  As stated above, I've done most of my assisting with friends - as they would rather spend hours on set with someone they already know and enjoy spending time with, instead of taking a gamble with someone new.

Most of my contacts I have met through working retail make up, some I have even met on MM.  Always present yourself professionally, online, and in person, no matter the size of the job.  I am ALWAYS on my A game even if I'm not working - you never know where and when you're going to meet someone important. 

That being said I will still send out random emails to people I have never met and admire the work of.  You need to have thick skin to work in this industry, so if/when you don't hear back, just let it roll off your back and don't be scared to try again.

I hope I didn't come across as a douche.   I'm just being really honest telling you what alot of people wouldn't .........

Again I can't stress if you are trying to assist a busy artist remember that they probably spend more time "on set" than at home , so try to have some sort if relationship with them

Anthony, you could never come across as a douche.

You said basically everything I was going to say, but in addition, there's the reality of just not having a lot of work to use an assistant on. It varies depending on the type of work and the budget. I do a lot of catalog and .com work. Film and TV is a totally different beast, and editorial is as well.

Lets put it this way as a breakdown:

in the last 18 months I've interviewed about 100 artists about assisting. Out of the 100, about 30 of them either had such great personalities that I didn't care about their skill level cause I knew I could mold them into something great, or their books were so good that they were obviously a benefit.

Out of those 30, around 7 have worked out. The rest have either not had schedules that worked with what we needed, had weird attitudes that popped up on set, didn't respond fast enough, decided this career wasn't for them, etc etc.

Out of the 7 that I really liked, that have great communication skills, are great on set, good skill level, etc, I just don't have enough work to give them. I've met quite a few artists from MM that I'd love to help out, I just don't have work for them and the artists that are loyal to me are the ones that get called back again and again and deserve to be the first ones called.

Bottom line as an example is that I worked 21 days on set last month and only had an assistant for 1 day. This month I will have 4 or 5 days for an assistant, in between 2 jobs.

Assisting is a vital part of the learning process, and please don't feel discouraged by this post, it's just the reality of what more experienced artists are facing when they get these emails.

What Anthony said is so incredibly true. You have to stand out or you are just another name on a list.

The only thing I could add to Anthony's great advice is,, be yourself. Be honest, open and transparent. Show them you have something to give but you will take direction.

And again, bang on, as said, you gotta be fun and not a pain in the ass.

Thank you guys so much all of this info is so helpful!