Auditions for SIDEWAYS by Rex Pickett


Sideways Audition

The Chatham Players will hold auditions for their 2024 – 2025 season opener, “Sideways” by Rex Pickett on Tuesday, June 18 and Wednesday, June 19 at 7 pm at The Chatham Playhouse 23 North Passaic Ave. Chatham, NJ at 7pm. Actors must check in to the auditions by 7:30pm. Production dates are September 20 – October 4, 2024 with rehearsals to begin early August. Christopher Peterson directs.

A wine-tasting road trip to salute the final days of bachelorhood careens woefully sideways as two friends hit the gas enroute to mid-life crises. The comically mismatched pair, who share little more than their history and a heady blend of failed potential and fading youth, soon find themselves drowning in wine and women. Emerging from a haze of Pinot Noir, wistful yearnings, and trepidation about their future, the two inevitably collide with reality. This play has been adapted for the stage by Rex Pickett from his 1998 novel of the same title, also released as a critically acclaimed film in 2004.

Director Christopher Peterson seeks a talented cast of 7 actors. Actors will be asked to read from sides provided below and at the audition. Cast must be available for the majority of August.  Missing select dates will be negotiable, but not full weeks.  Advance notice is required. Mandatory dates are September 14 – 19 for Tech Week and September 20 – October 4 (Three Weekends) for Performances.

Character Breakdown

* Miles (Male) Late 30’s - Dumpy and disheveled, self-absorbed and depressive. He is very literate, even philosophical, with a highly developed vocabulary and sense of irony. He is a true intellectual, an unpublished novelist and introvert, he can be frantically obsessive at times, becoming wildly flamboyant and uninhibited, particularly when drunk. His mood swings are comically extreme.

* Jack (Male) Late 30’s – A tall, handsome, well-built actor overly conscious of his own charm and sex appeal. There’s something smarmy and glib about Jack, something of the used car salesman about him, and yet he's impossible not to like. His boyish appetites and high spirits are endearing, almost contagious, although he's obviously a bit of a "dim bulb." He's like a fraternity "bro" who never grew up, cocky and domineering, without a shade of insecurity or self-doubt.

* Maya (Female) Mid 30’s - Warm, lovely, and soulful. There is an emotional vulnerability and a heightened sensitivity about Maya that should make the audience feel protective of her. She's clearly been hurt in the past and struggled to get her life back on track. But she's an intelligent, well-read, and deeply reflective person who has reason to be proud of her hard-won independence. She may be lonely at times, even a little sad, but she's made her peace with life and achieved something bordering on wisdom.

* Terra (Female) Mid 20’s to 30’s - Remarkably sexy, fiery and impetuous, self-confident, strong willed, unapologetic, and she's aware of the effect she has on men. There's an undeniable swagger about Terra, a defiant toughness which gives the impression that she's "game" for just about anything, but underneath the "bad girl" pose is a fragile, insecure person who's also been hurt by men in the past.

* Phyllis/Evelyn (Female) Early 60’s-70’s - An actor capable of playing both an ordinary, comically unsophisticated and mundane mid-western mom who drinks too much, as well as a slick, hard-nosed, straight-talking New York City editor.

* Lissy/Brenda/Victoria (Female) Early to Mid 30’s - An actor capable of playing both a pert, savvy working-class type, as well as Miles' cold, judgmental, upper-middle-class ex-wife.

* Brad/Chris/Charlie/Tasting Room Manager (Male) 30’s to Early 50’s - An eclectic group of wine country workers.

The Chatham Players have an open call casting policy. ALL roles are open, none are precast, and everyone is encouraged to audition. Any questions, please call Gus Ibranyi at (201)-563-0362 or email  For directions or additional information, please visit