Prolific Joe DiPietro says a writer only grows when he challenges himself and that he never wants to write the same play twice.

His earnestness is proven by the four — count ’em, four — pieces the New Jersey native currently has in production. “Ernest Shackleton Loves Me,” at New Brunswick’s George Street Playhouse through May 17, is a fanciful two-actor, multi-character musical that uses magical realism to unite a contemporary woman with the eponymous Antarctic explorer who died in 1922.

“Living on Love,” opening Monday at Broadway’s Longacre Theater, is a screwball comedy adapted from Garson Kanin’s play “Peccadillo,” about a jealous opera singer who seeks revenge on her philandering husband and stars Met diva Renee Fleming in a role that requires more acting than singing.

His 2010 Tony-winning musical “Memphis,” about the breaking of color lines in popular music, runs at Philadelphia’s Walnut Street Theater from May 12 to July 12 with Christopher Sutton playing the deejay who defiantly brings black artists to radio.

And an historical drama, “The Second Mrs. Wilson,” that DiPietro says is Shakespearean in scope, opens in three weeks at New Haven’s Long Wharf Theater.

Add to all of this DiPietro’s breakthrough play, “I Love You, You’re Perfect, Now Change,” a staple of regional theater worldwide, and his book for the recent Broadway hit, “Nice Work If You Can Get It,” and it’s obvious why DiPietro is one of the few writers who can comfortably spend his time devising plays without having to teach or look for writing assignments to make financial ends meet.

The years DiPietro has spent in theater, and the success his plays have had, gives him entree to producers and artistic directors many writers would sacrifice limbs to enjoy. When “Ernest Shackleton Loves Me,” which started life as a one-woman show, had an encouraging production in Seattle last April, DiPietro called George Street’s David Saint, known for championing new works, to introduce him to the piece and propose it for George Street’s current season. No agent or other go-between was involved.

Producers approach DiPietro with projects. “Living on Love” needed someone to adapt Kanin’s script, and DiPietro, who as a rule puts entertaining his audience above all, was asked if he would be interested. “Memphis” came about when DiPietro was approached to do a musical about an actual deejay and suggested his story be fictionalized to give it more facets. His partner as composer in that venture is David Bryan, the keyboard player for Bon Jovi and DiPietro’s collaborator on a musical in progress. “The Second Mrs. Wilson” is DiPietro’s own conception and, he says, a major departure from much of his work to date.

For “Ernest Shackleton Loves Me” DiPietro teams with the song-writing trio GrooveLily’s Valerie Vigoda and Brendan Millburn for a musical he says blends his uptown approach with Vigoda and Millburn’s downtown style.

“Uptown,” DiPietro says, “appeals to wide audience. It’s polished and accessible. Downtown is experimental and edgy. It can be a little rougher and less defined. It’s more raw. The combination is exciting and very much illustrates what live theater can do that is more difficult to accomplish in movies or on television.

“In the musical Valerie plays an experimental composer who lives a modern, unconventional life in Brooklyn. Her life is always in some kind of turmoil, and she’s frustrated by numerous things, including her boyfriend leaving her for some undetermined time to go on tour with a Journey cover band. She wants more romance, and she centers on the adventurer Ernest Shackleton as her fantasy lover. The musical goes through time to make that romance happen. It is not your usual fare.”

DiPietro thinks Vigoda is an extraordinary performer and says, “She not only enacts the lead character, but she is the show’s lyricist and plays several instruments, including the electric violin for which she’s known. The male lead, Wade McCollum, plays several characters but primarily Ernest Shackleton. Valerie and Brendan’s music is contemporary but geared to let the characters come through. There’s empathy in this piece, and we see a lot from a young person’s point of view.”

Theater is DiPietro’s metier. He has been asked to write for movies or television, but he says he prefers the connection to the live audience you can’t get from the media.

“I also enjoy the collaboration. Writing is the lonely, solitary activity it’s usually portrayed as being. The theater is incredibly social. You’re working with so many people on so many aspects of a production. It’s exciting, especially for someone like me who is always engaged in the world but always remains a half-step back to observe and analyze everything around me like a writer does. I can be outgoing, but I’m not really gregarious or extroverted. I can have fun and occupy myself sitting quietly and watching how people behave and listening for what they say and how they say it.”

DiPietro doesn’t remember when he started writing. “I would say I always liked stories, but that I started writing as a habit when I was 10 or 11. I grew up in Oradell, New Jersey, near Paramus. I was a typical idealistic suburban child. My parents were second-generation Italians who believed in exposing their children to music and culture, an Italian passion.”

Yet there was another benefit to where he grew up. “Being so close to New York, I was taken regularly to see Broadway shows, about five or six a year. The first was ‘1776.’ I was mesmerized. It’s not like the show has a surprise ending. You know the Continental Congress will unanimously vote to announce the Declaration of Independence. But the suspense was real, and an historical event became immediate and ingrained. I was hooked. I still remember the tension before that last vote was cast. I wanted to be a part of that. I wanted to create that kind of excitement. (Yet) I did not stop being a kid. I played soccer and other sports, hung around with my friends, and did boy stuff. But I also wrote, mostly short stories but some plays. Being a good Jersey boy, I went from high school to Rutgers (Class of 1984), where I got my degree in English.”

About his current success he says, “I did not become a produced playwright overnight. I worked in advertising and lived the fabled writer’s existence. I did my job during the day, and I wrote at night. By this time, I was only writing plays, and I would send them out to various theaters and artistic directors who generally ignored them. I received no response at all.”

He may have been ignored but he wasn’t discouraged. “I love the act of writing and my work improving. For seven years I sent out plays and sketches to various places. Eventually a couple of small theaters liked my work, and I began getting a small number of productions that were encouraging enough for me to continue. Some sketches I wrote were performed at dirty downtown bars. That was also encouraging because I saw what got an audience’s attention. Meanwhile, I was learning to write and was writing more and more intently.

“The turning point came when I was accepted to the National Playwrights Conference at the Eugene O’Neill Center in Waterford, Connecticut. Lloyd Richards, who was a mentor to so many, August Wilson in particular, was still the head at the time, and I learned a lot. The most important lesson was about rewriting. The piece I was working on was ‘Over the River and Through the Woods,’ a play about my grandmother’s early life in Hoboken, New Jersey. I realized something I always knew instinctively. A play does not come out of a writer’s printer in perfect form. It has to be rewritten and molded and made to entertain an audience accessibly. Now that I have worked with so many companies on so many productions, I am attuned to the actors’ voices and the lines and passages that are less accessible than others. I look to hone my work to make it fit the artistic needs of all concerned. That is an important thing for a playwright to know.”

It was at the O’Neill in 1995 where he first got significant attention with “I Love You, You’re Perfect, Now Change.” The following year it opened at New York’s Westside Theater. “I was elated. An off-Broadway producer saw something in my work and decided to give it a major production in a well-known theater. If the show ran 90 days, I would have been happy. If it ran for six months, I’d have been beside myself. ‘I Love You, You’re Perfect, Now Change’ was at the Westside for 12 years. It’s been produced everywhere. Several of my plays have. There are 15 or 20 of them by now. It’s interesting when I receive programs from productions in Japan and Norway and other places. I always wonder how they translate and how accessible they are.

“I Love You, You’re Perfect, Now Change” did something else for DiPietro. “It provided income enough that I didn’t have to have any job other than writing for the theater. I was free to concentrate on what I wanted to do. ‘Over the River and Through the Woods’ was produced two years after ‘I Love You,’ and I have worked steadily since.”

Born in 1961, DiPietro began reading plays seriously in his teens, which would have been in the ’70s. He says his influences were Joe Orton, Neil Simon, and Arthur Miller, the last of whom he said is great to study for structure. “I also read a lot of the edgier plays younger writers were producing.”

Although committed to writing for the theater, DiPietro is a movie buff who says he learned a lot about drama from the black-and-white movies of the 1950s, such as “Sunset Boulevard,” “All About Eve,” “Some Like It Hot,” and “The Apartment,” three of which are directed by Billy Wilder. “Those movies were witty, perceptive, and complicated. I like them especially because they depict adults being adult,” he says.

DiPietro has a reputation of putting entertainment first, and he says is proud of that. “My first job is to entertain the audience. I think that can be done with integrity and depth, and that I remain accessible without condescending,” he says.

An out gay man who likes to keep his personal life private, DiPietro’s success is witnessed intently by his parents, Lou, a retired banker, and Jean, a homemaker, who now live in Hamilton.

“You can go two years with no activity beyond constant writing and then be faced with an avalanche of work. This is one of those times with ‘Ernest Shackleton Loves Me’ and ‘Living on Love’ opening back to back, and ‘The Second Mrs. Wilson,’ which is so different from anything I’ve done, premiering right after them,” DiPietro says. “The theater is strange.”

Ernest Shackleton Loves Me, George Street Playhouse, 9 Livingston Avenue, New Brunswick. Through Sunday, May 17. $28 to $65. 732-246-7717 or www.georgestreetplayhouse.org.

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