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Williamstown Theatre Festival
Back in 2008, I was an apprentice at the Williamstown Theatre Festival. Williamstown is an annual festival that puts on several plays and musicals up in Williamstown, Massachusetts (home to Williams College.) 
The apprentice program is notable for having numerous famous (acting) alums and is generally considered a huge resume get for actors in the New York area. I thought I’d write a blog post summarizing some of my experiences which hopefully might be helpful for anyone considering the program.
I was a late-comer to acting — having taken my first acting class in 2007 shortly after I went on sabbatical while at Google. Before this, I had never acted in anything. I quickly became obsessed with acting and learning and started to take all sorts of classes — from acting to improv to movement to monologue workshops to anything and everything that I thought might help me. 
Around this time, I saw Steppenwolf’s production of “August: Osage County” and to this day, it’s the finest theater production I’ve ever seen (though I never did see “Hamilton”.) I was enthralled by Steppenwolf and longed to somehow be a part of that community. It turns out that they have an annual summer program so I applied. However, I was also doing some career coaching at a place called Capes Coaching at the time — and I believe Williamstown must’ve came up when I mentioned that I was applying to Steppenwolf.
Now, I don’t want to overstate Williamstown because I am an alum, but *everyone* I talked to basically said Williamstown was the gold standard. That that was the place to go. I thought this was all well and good, but I wanted to go to Steppenwolf! It was 12(?) weeks of acting class with some of the finest actors I knew and it seemed exactly like what I was looking for. The Steppenwolf essay practically wrote itself. I honestly was a bit unclear exactly what the program at Williamstown was like.
When the time came, I got into Williamstown… and I wouldn’t hear from Steppenwolf for another week. Williamstown wanted an answer — and frankly, I think they were unaccustomed to hearing anything but an immediate yes. The people who were advising me (including one very accomplished theater person) basically told me, “We don’t care what you think you’ll get out of Steppenwolf. The only thing folks in NYC care about is Williamstown. That on your resume, alone, will get you into casting offices.” I *think* I called Steppenwolf and they wouldn’t give me an answer early. I think if I had gotten in to both, I would’ve gone to Steppenwolf, but that wasn’t an option. So I accepted Williamstown and withdrew from Steppenwolf. Boo.
Now, the first thing I should say about Williamstown is it’s not really any sort of acting-training program and more like acting camp. Our days (and nights) were filled by working on crew positions for the festival — everything from picking up trash to ironing clothes to setting up lights to helping build sets to doing backstage work during an actual production. Some of us (and I have no idea if that # is like 5 or 25) got the chance to either work as background actors on the productions and a very small # got the chance to actually have a small part in some of the productions.
At least based on my recollection, there were 3 actors in the apprentice program (out of 80? 90?) who seemed to be favored by the productions / higher ups / etc. 
They were:
Ian Harding — who went on to star on “Pretty Little Liars”
Andrea Syglowski — who later graduated from Julliard
Kerry Malloy — who I’ve seen pop up on “The Wolf of Wall Street” and “House of Cards”.
One thing I should note is that the mainstage productions had generally well-known actors (when I was there this included folks like Bradley Cooper, Wendell Pierce, and Kate Burton but also had folks who were quite accomplished but were widely unknown) and then there was a group of actors who were part of another company (this might be their non-equity company but I honestly can’t remember). For the folks in the non-eq company, it seemed like they spent their days focused on their own productions (i.e. they spent their time acting) which were later put on on side stages and were always extremely well attended (and often by the actors from the main productions too). When I was there, I believe this included folks like Heather Lind (AMC’s “Turn”) and Aya Cash (“You’re the Worst”) but obviously at an earlier stage in their respective careers.
I believe that the apprentice program is thought of as a feeder program into the non-eq company.
In full disclosure, I did not like my time at Williamstown. I don’t blame Williamstown at all for this. In fact, I would argue that it seemed like *everyone* else was having an amazing time. I think my unhappiness was due to a number of reasons. One — I had wanted to go to Steppenwolf. Two — I was already older than most of the apprentices (who were generally in college and I had already worked for several years and lived on my own) so going back to living in a dorm situation was a little bit of a system shock. Three — I wanted to spend my time on acting-related things and for the vast majority of the apprentices, that was not the case (and I was not the only person who felt this way). But again — if you’re thinking about Williamstown, it’s theater camp. If that sounds like fun to you, you’ll probably have a blast.
Now, of course, having access to such accomplished actors in various stages of their career is invaluable. I’ll always remember the grace with which Bradley Cooper treated me (something which I cannot say for some of the other actors on whose productions I crewed on). (I actually had no idea who Bradley Cooper was back then btw — he had not done “The Hangover” yet though this was after “Wedding Crashers”.)
Wendell Pierce (I had not seen “The Wire” yet and this was sometime toward the end of their run) — and he couldn’t have been kinder or more fun to hang out with. Also, by the time I finally got a chance to watching “The Wire” (now one of my favorite shows of all time) — I still can’t believe that I got to hang out with Bunk and can now even email him and he’ll get back to me. 
Gaius Charles — Smash Williams on Friday Night Lights! I’ll never forget what Gaius did for me. He just came up to me on the street and said, “Hey, you want to grab a coffee?” I hemmed and hawed b/c I was so shy and he goes, “You want to be an actor right?” “Yeah.” “Then grab a coffee with me. I’ll tell you everything I know.” And he did. He spent like an hour and a half with me and answered every question I could think of. Beyond gracious. Paying it forward. What a guy. 
So yeah, things like that are completely priceless. And you get access to those types of people because they’re just hanging out (maybe sometimes bored) like you. You’ll see them walking to the store or a restaurant of wherever because there’s not a whole lot of places to go in Williamstown! You can approach them in a way you really can’t approach them elsewhere.
By the way, if you’re an ambitious actor earlier in your career, you’re probably wondering, “But did it help you with your career?” Well, sort of. The one thing Williamstown really gave me was a crystal clear understanding that I did not want to do theater. Which I’m sure sounds strange coming from an actor — and something which I shied away from saying for a long time. But I like film + TV. That’s what I watch, all the time. I really only got comfortable with that fact after working with Jenny Slate. At lunch during a production, one of the other actors asked her if she’s ever done theater and she said something to the effect of, “No, I don’t really like theater.” Every since then — I figured if it’s good enough for Jenny Slate, that’s good enough for me. So my manager stopped submitting me for theater productions — even when theater productions reach out to me individually, I turn it down. I’m flattered they’re interested, but I don’t like the rhythm, the lifestyle, and I really like the output of film and TV. 
Because of that realization, I moved out to Los Angeles almost immediately after getting home from Williamstown. New York is a terrific town. There’s tons of film, TV, and theater. But I always felt a strong push in NY towards theater. Like that’s where the real actors were. And I felt among the actors I knew — most everyone, deep down, wanted to do film and TV, and on the surface, claimed what they really wanted to do was theater. Which is fine to me. But I grew up watching Friends and ER. If I grew up going to Broadways shows every weekend, maybe I would have different ambitions.
For the first few years out in L.A., I had the Williamstown credit on my resume — which I’m pretty sure did nothing for me out in L.A. I would estimate that close to no one in Los Angeles knows Williamstown. I do think, however, that that is different in New York. But I don’t think it’s the golden ticket people make it out to be. I think it can be an important credit early in one’s career and there are probably casting offices who will bring you in b/c of it. (and if you become part of the family — going from the apprentice program to the non-eq company then maybe to mainstage productions — you’ll make powerful connections, probably get your manager or agent from there, etc. But the percent of apprentices who go through that path is probably <10%. It’s possible, but unlikely.)
As I said, I did not enjoy my time there, but I do think that most everyone else really did seem to love it and with time and reflection, I feel really fortunate for what I learned and got exposed to while there. Even some of the smaller moments — like how to carry oneself or small pieces of acting advice when I ran into an actor I admired. 
If you go, enjoy your time and take advantage of everything Williamstown has to offer. Because it has a lot to offer.