Bachelorette takes place in a fancy Manhattan hotel room (beautifully realized by set designer Andromache Chalfant), the night before the wedding of Becky (Carmen M. Herlihy) to her wealthy fiancé. However, rather than focus on the bride, Headland charts the misadventures of her maid of honor, Regan (Tracee Chimo), and two other longtime friends -- Katie (Celia Keenan-Bolger) and Gena (Katherine Waterston) -- who may not have even been invited to the nuptials.
Regan, Katie, and Gena have the hotel suite to themselves, while Becky is off with her fiancé. It's clear that the three women don't even really like Becky, and have mostly disparaging things to say about her -- particularly regarding her weight. (However, a sight gag involving two of the women trying to fit into Becky's enormous wedding dress is one of the few missteps of the production, as the dress proves way too big to even fit on Herlihy.)
Regan has also invited two men she has just met -- Jeff (Eddie Kaye Thomas) and Joe (Fran Kranz) -- to join the party. Sex, drugs, and alcohol form a potent mix, and the evening starts to unravel early on -- before spiraling even further downhill.
Headland traffics in archetypes, but fleshes out the roles sufficiently to make them distinctive. Her spot-on dialogue is alternately crass and insightful. Some of the pronouncements -- particularly between the three bachelorettes prior to the arrival of the boys -- are wickedly funny and more than a little mean-spirited.
Chimo is riveting as Regan, crafting an icy cool façade that only partially masks a raging torrent of emotions underneath. Keenan-Bolger initially plays her character's self-pity for laughs, and then goes deeper to show her pain and loneliness. Waterston displays many sides to Gena -- from her wild partying to genuine strength and friendship when things start to get out of control -- but is perhaps most effective in a quiet moment of vulnerability after Regan discloses a secret from Gena's past.
Thomas is equal parts charm and smarm, and his interactions with Chimo are some of the funniest -- and certainly the sexiest -- moments in the production. Kranz's Joe is the most sympathetic character in the play, and the actor perfectly captures the awkward mannerisms that make this sad stoner so endearing. Herlihy has the least amount of stage time, but makes a good impression as the sensible, yet understandably exasperated Becky.
Director Trip Cullman expertly guides his cast through the play's various shifts in tone and mood. Who has power over whom changes constantly as the action progresses, and yet character relationships and motivations always remain clear.
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