NEW CANAAN — Paul Simon ended his recent North American tour in New York last Friday with a cliffhanger.

In comments picked up — and parsed — by news outlets around the world, Simon suggested to the New York Times that he was contemplating retirement.

The 74-year-old New Canaan resident and pop music icon may have already hinted as much on his newly released album, “Stranger to Stranger.”

There is little instrumental accompaniment on “Insomniac’s Lullaby,” the album’s final track. In this poignant, acoustic plea for sleep that won’t come, Simon delivers the refrain, “Oh Lord, don’t keep me up all night/With questions I can’t understand” in a strong, youthful voice that sounds surprisingly similar to the one that once sang “Hello darkness my old friend.”

But six decades separate the two voices and, especially after Simon’s recent comments, it seems the questions keeping him up at night may well concern his future in the music industry.

“Showbiz doesn’t hold any interest for me. None,” Simon declared on the eve of his appearance in Forest Hills, Queens, where, notably, he spent his formative years and began his legendary, hot-and-cold collaboration with Art Garfunkel.

Leading up to a European tour later this summer, such remarks could be seen as a way for the lion in winter to ensure that his “farewell” tour is well attended. But Simon is far from the typical septuagenarian pop star.

“Stranger to Stranger” has attained best-seller status and received nearly unanimous critical acclaim since its June release. For the week of July 9, the album was ranked 43rd on the Billboard Top 200 Album chart and his Forest Hills performance was hailed as “triumphant” by Rolling Stone.

In the opinion of New Canaan resident Peter Bush — radio DJ at 95.9 The Fox and a longtime Simon fan — if the retirement rumors are true, Simon has picked the perfect time to make his exit.

“If he goes out now, he goes out on top. The thing is great. It’s an album by a 74-year-old legend competing with Kanye and Beyonce,” Bush said over the phone last week.

“He hasn’t had an album in years. This album comes out and it’s a smash. A lot of these classic rockers, their albums just don’t sell. But here’s Paul Simon defying all odds.”

Since early hits in the 1960s like “The Sound of Silence” and “Homeward Bound,” Simon has managed to remain firmly at the center of the pop universe, both as a member of Simon and Garfunkel and, after their split in 1970, as a solo musician.

Unlike a broad swath of his music industry contemporaries, Simon has demonstrated a passion for reinventing himself aesthetically and a knack for assimilating striking new sounds and musical ideas.

From his early days harmonizing with Garfunkel under the moniker Tom and Jerry, to the Afro-Brazilian percussive influence on 1990’s landmark “The Rhythm of the Saints,” Simon has transcended genre boundaries and moved nimbly in and out of radically different realms of musical expression.

In New Canaan’s music community, regard for Simon’s consummate musicianship runs high.

“Paul Simon changed everything, and people came along for the ride. He’s a trendsetter,” Bush said. “He’s an icon. I think he’s one of the all-time great songwriters of any genre. But he’s also human.”

Jim O’Neill, of New Canaan Music, said he remembered listening to Simon and Garfunkel as a child when his baby sitter would bring over records.

“Through his career, he’s always been a great songwriter,” O’Neill said.

Phil Williams, owner of New Canaan Music, added: “I’ve been a big fan of his my whole life. I wish he wouldn’t stop, for selfish reasons. But I understand everybody needs to take a break sometime.”

Despite moments of playful exuberance — especially on tracks like “Cool Papa Bell” and “In a Parade” — the “Stranger to Stranger” album may be interpreted as an artist’s wistful rumination on a career almost at an end.

Instrumentals such as “The Clock” and “In the Garden of Edie,” the latter of which was written for Simon’s wife, Edie Brickell, serve throughout as counterpoints to songs with larger sounds and lighter moods.

Even in more upbeat songs such as “Wristband,” which tells the story of a musician denied entry to a venue at which he’s supposed to be playing, the lyrics often assume a darker tone and address graver issues than Simon’s signature sweet delivery might suggest.

The result is an album that changes tones and shifts musical directions multiple times within its richly textured 37 minutes, before ending on “Insomniac’s Lullaby,” an expression of a desire for rest unfulfilled.

“If it is time to call it quits,” Bush said, “no one deserves to make that call more than him.”;