NILES — No playwright has a better history of laugh-delivering dependability than Neil Simon.

That’s why he remains a community theater staple nearly 65 years after the debut of his first play on Broadway.

Some have aged better than others, and “Last of the Red Hot Lovers,” which opened Friday for a three-weekend run at Trumbull New Theatre, doesn’t hold up quite as well as some of Simon’s more frequently produced works. A talented duo mines plenty of comedy from the master’s script, but it will play best with those who can watch it through late 1960s eyes and sensibilities.

The three-act comedy is about a middle-aged man, married restaurant owner Barney Cashman, who’s had a nice life but is starting to ponder his own mortality and wonder about what he’s missed out on while being a faithful husband.

Each act focuses on his efforts to add a little excitement by trying to have a tryst with a different woman on a weekday afternoon at his mother’s apartment.

The first act is by far the funniest as the inexperienced, fumbling Barney encounters a very experienced, no-nonsense partner in Elaine Navazio. Imagine Mrs. Robinson from “The Graduate” with a middle-aged Benjamin Braddock.

The show’s comedic tour de force is Barney delivering an impassioned speech about just wanting to have a passionate moment with another woman while the very willing woman just a few feet behind him shifts from inviting body language to exasperation to boredom and searching under the couch cushions for cash. It’s a great bit of physical comedy from Amy Burd, made all the more effective by Thomas Burd’s obliviousness to what’s going on behind him. Director Robert Spain’s work with the cast here is top-notch as they build and add layers to the bit.

Amy Burd plays all three women who come to the apartment to meet Barney and convincingly creates three distinctive characters. Thomas Burd is playing the same character throughout, but he skillfully handles Barney’s evolution as he becomes more adept, if not more successful, in his pursuits.

In the second act, she’s a flighty, aspiring singer-actress with an attention span that careens around like a pinball as she spins conspiracy theories about a kidnapped dog and a famous author while hinting at fantastically bizarre sexual encounters with everyone from a lesbian Nazi vocal coach to a porno movie screenwriter.

Her rapid-fire ramblings and off-key singing generate laughter, but the middle segment also is the most dated of the three acts. The Barney-gets-high-for-the-first-time scene plays like dozens of bad sitcoms and mediocre movies over the years. Maybe Simon wrote it first — I don’t know — but Spain and the actors can’t overcome the herculean task of making that material feel fresh. It plays like drug humor written by someone who never inhaled.

The third act is more poignant as Barney invites one of his wife’s friends, Jeannette Fisher, a lithium-popping severely depressed woman whose therapist has determined she’s only been happy for only 8.2% of her life. Jeannette hides behind her purse like it’s a bulletproof vest she’s trying to use to protect her from life’s wounds, and Barney’s determination to get her to PUT DOWN THAT PURSE provides the few comedic beats in a third act that, like its characters, is more melancholy.

Tom Hitmar’s set is simple and serves the needs of the play and the set decoration creates a believable facsimile of an older woman’s late ’60s apartment.