Melissa Errico Sings Out the Summer at SAC

Labor Day is officially on the horizon, and here on the East End it has been a season filled with the sunny sights and sounds of summer. But as evenings noticeably shorten, the weather grows more intense and the mood shifts subtly — thoughts of introspection and reflection emerge as we sense the turning of the planet (and the leaves) and settle in for shorter days ahead.

Contradictory emotions, like those inherent in the changing of the seasons, are something that Broadway singer and actress Melissa Errico understands well. As one of the preeminent interpreters of the music of late, great composer and lyricist Stephen Sondheim, she recognizes the paradoxes in the human condition that Sondheim so eloquently embraced.

“Sondheim is full of contradictions,” she said. “None of us is simple — we’re all made up of contradictions, we’re either hopeful or falling to pieces.”

Sondheim died in November 2021 at age 91, and Errico compares the depths of his musical insight to psychoanalysis of the 1960s or 1970s. If he had written “Oklahoma,” she quipped in a recent phone interview, his version of the opening number might have gone, “Oh what a beautiful morning (after a terrible night).”

“Historians of musical theater will argue about Sondheim’s place for decades. For me, as a performer — and ,yes, writer, too — the great leap was the way he allowed ambivalent and complicated emotion into the life of the American musical theater,” she explained. “I call it the ‘Sondheim Comma’ — the way he always asserts one emotion and then its opposite. ‘Marry Me, a Little,’ ‘Sorry, Grateful,’ ‘Good Thing, Going.’

“You even saw the comma in the twisted, ironic expression on his face,” she added. “The songs are always turning in on themselves, offering new complexities of feeling. That’s why we never come to the end of Sondheim’s art.”

No matter what mood East End audiences might be in on September 1, there will no doubt be “A Little Night Music” for everyone when Errico comes to close the curtain on the season with a show at Southampton Arts Center. Titled “Melissa Errico Sings The Summer,” her concert will feature stories about her life on Broadway alongside numbers from songwriting teams like Lerner and Loewe, and Rodgers and Hart, beloved tunes from The Great American Songbook and, of course, deeply moving offerings from Errico’s two long-term, beloved collaborators — Sondheim and composer Michel Legrand (who died in 2019).

“This concert is showtunes and jazz standards — everything fun and sexy that comes to mind,” she said. “I try to bring every summer sight and sound to this show. To me summer, is not just about dreaming while relaxing, but also taking stock.”

Few songs reflect the melancholy of the season’s end like Legrand’s hauntingly beautiful classic “The Summer Knows” (the Academy-Award winning theme from “Summer of ’42”) with words by Marilyn and Alan Bergman, and it’s one that Errico will most certainly sing on September 1.

“The lyrics say, ‘one last caress, it’s time to dress for fall,’” quotes Errico. “It’s a Streisand song and it’s mine too — it’s one more chance to be sexy, silly and sassy.

“I’ll also be singing music by Cole Porter, Jule Styne, Jobim and, of course, Sondheim,” said Errico. “Everything that makes me feel like summer and will sweep us away.”

It’s not just the older songs that inspire her. Errico added that she also loves the “second” American songbook by singers and songwriters like Joni Mitchell, Randy Newman and James Taylor.

“I have been singing those songs all my life, too,” she explained. “And in recent years I’ve discovered myself as a ‘jazz adjacent’ singer and maybe even recently, as in my appearance with George Benson’s band at the Montreal Jazz Festival, as an honest to God jazz singer. That was definitely a highlight of this year. So, all of those paths converge in a single clearing, which is where I live now.”

Speaking of where she lives now, this past February, Errico released her latest album, “Sondheim In The City” on Concord Records. The album features Sondheim’s songs about New York City, a place Errico loves as well. While she describes her 2018 record “Sondheim Sublime,” as one that is essentially inward facing, reflecting the composer’s wisdom and philosophies, this new album is a celebration of the musical legacy that he has left behind.

“Soon after Sondheim died, I felt New York suffered a great loss. He was the figure who represented it the best,” she said. “There were few musical theater actors who wouldn’t be terrified knowing he was in the audience. That era is ending. I felt his passing. If I call ‘Sondheim Sublime’ inward, this one is outward, a celebration and reopening of the city after the pandemic, in all its brilliant frustrations.”

Errico’s first personal encounter with Sondheim came in 2002 as she was preparing for the role of Dot/Marie in his musical “Sunday In The Park With George,” which was presented at the Kennedy Center in Washington, D.C. The show was produced as part of a summerlong Sondheim Celebration in which full productions of all of his works were performed.

“As we were setting our dance together, I proposed playing the opening scene nude in the bath, which wasn’t what he’d written,” Errico recalled. “I didn’t have enough experience then to know that you weren’t supposed to propose changes like that to Sondheim, but he took it in stride, liked the idea and gently changed a couple of lyrics to make it work better. He was a great man in his talent, and a fine one in his generosities.”

Years later, as she was working on “Sondheim Sublime,” she engaged in hundreds of emails with the composer, which further illuminated her understanding of the man and his work.

“Stephen Sondheim was a wonderful friend and for me, a mentor of a kind,” explained Errico. “I don’t pretend that we were intimate, but when I was working on my Sondheim record, he offered me nearly 100 emails on every kind of question, from recommending little known songs — like ‘Isn’t He Something’ from the troubled show ‘Roadshow,’ to giving me strict orders to sing his songs as written — and then gleeful permission to become a ‘girl singer’ right after and go a little wild interpretively.

“He was deeply kind, but said things with an acid tongue,” she added. “One time he found me too self-deprecating on stage. He said, ‘Stop it. That’s the most negative quality.’ He said ‘I’m the champ of it and I don’t want competition.’”

In keeping with the traditions of fall, the upcoming performance at SAC will be something of a homecoming for Errico, who has been singing on East End stages since the early 1990s when she first performed at Guild Hall as a college student. She has performed at Guild Hall more than a dozen times in the years since, as well as on the stage of other venues, including Bay Street Theater (where she presented her show “Let Yourself Go” just last August). Joining her at SAC for the upcoming show will be renowned jazz pianist Tedd Firth, who plays all over the world, and an ensemble.

“We do have a jazz ensemble,” confirmed Errico. “I take it seriously. It’s not just a summer show.”

Melissa Errico presents “Melissa Sings The Summer” at Southampton Arts Center on Sunday, September 1, at 7 p.m. Tickets are $75 to $125 at southamptonartscenter.org. Southampton Arts Center is at 25 Jobs Lane, Southampton.