The Loneliest Time of the Year

Joshua Conkel possesses one
of the most deliciously off-kilter imaginations currently being put to use in
New York. His MilkMilkLemonade
(which New York Press named the
Best Off-Off-Broadway show of 2009) was a refreshing rebuttal to the usual slew
of sloppy gay plays. His Lonesome Winter, co-written with Megan Hill, proves that MilkMilkLemonade wasn’t a fluke.

Lonesome Winter also reveals a much bleaker worldview. How much of
the show is Conkel and how much is Hill is up for debate, but the combination
of the two results in some delightfully excruciating comedy. Hill stars as
Winter Lipschitz, a compulsive shopper who feeds her habit by working at the
Shopping at Home network and takes cat-food sandwiches to work. Friendless and
alone, Winter has only her cat, Sparkles (Conkel, made up to look like a member
of a Cats bus-and-truck tour),
for company. But Sparkles turns out to be less a purring companion and more of
a claws-out frenemy, prone to ordering Winter to look at herself with the force
of Bette Davis reminding Joan Crawford that she’s still in that chair in Whatever
Happened to Baby Jane?

Things take a turn from
Cathy comics to Falalala Lifetime with the miraculous appearance of life coach
Debbie Metzger-Bolger (Nicole Beerman), who appears with all the fanfare of the
Angel in Angels in America.
Debbie, you see, isn’t quite what she claims to be. But she’s determined to
make this the best Christmas that Winter has ever had, though turning Winter
into a functional member of society requires an attempt at suicide; numerous
montages and karaoke performances; and what seems like the world’s saddest
Christmas party. Along the way, Winter reconnects with her older sister Avery
(Kirsten Hopkins) and makes a new friend in fellow co-worker, Bobby (Nick
Lewis, making hay of his stoner character).

Like MilkMilkLemonade, the script for Lonesome Winter also serves as a blender for pop culture
references, from Hoarders to the
hand models on home shopping networks. But unlike so many young playwrights,
Conkel and Hill refuse to let their satirical targets overwhelm their vision.
Exquisitely cast and cleverly directed by Meg Sturiano in a way that minimizes
the pain of the numerous set changes (a stellar music selection helps; who can
be bored when “Last Christmas” is playing?) and prevents the montage sequences
from devolving into downtime, Lonesome Winter never shies away from the loneliness of the holiday
season, even as we laugh at poor Winter and Sparkles.

Sturiano embraces the pain
of the script; under her guidance, Hill gives a mesmerizing performance that is
somehow equal parts silent pain and quivery-voiced jokes. She’s a funny-sad
woman, and that dichotomy is clearly both Conkel’s and Hill’s sweet spot.

Conkel and Hill also
smartly refuse to move on when things get painful. A late-in-the-show scene
between Bobby and Winter goes on and on, keeping us on the hook even as we want
to look away. And Sparkles never does have a redeeming change of heart, while
by play’s end, Winter’s future looks only slightly less depressing. A
last-minute reprieve proves that Conkel and Hill aren’t engaged in a
sado-masochistic relationship with their characters (and audience), but even as
the Christmas spirit blooms forth on stage, the playwrights’ vision is still
happily askance.

Plays like Lonesome
Winter and playwrights like these
are exactly what New York needs right now. In a week that saw closing notices
posted for The Scottsboro Boys
and Bloody Bloody Andrew Jackson,
two shows that required the audience to (of all ghastly things) think, seeing a
play that doesn’t shy away from reveling in darkness outlined by slivers of
hope is absurdly refreshing. Absurd because plays that don’t coddle the
audience are in short supply these days. Take my word for it that Lonesome
Winter is the funniest feel-bad
show of the holiday season.

Lonesome Winter, through Dec. 19, Under St.
Marks, 94 St. Mark’s Place (betw. Ave. A & 1st Ave.), 212-868-4444; $18.