For all his plain-speaking, down-homey affect, Harry Connick, Jr. remains something of a mystery. While it’s easy to appreciate his dedication to New Orleans’ recovery or his uncanny appropriation of Sinatra’s swing, his movie career is curious. Reliably charming, he shows a talent for playing characters who seem much like himself, and bending each context to his amiable will. No matter the context — Copycat, Independence Day, Basic, even TV’s Will & Grace — Connick is beguiling. This even when the projects are emphatically not.
Case in point: P.S. I Love You, a miserable holiday romance ostensibly starring Hilary Swank as worrywart Holly and Gerard Butler as her gorgeous husband Gerry. As the movie begins, these two are in serious love, though their marriage is marked by disagreements, financial anxieties, and hopes for the future. During a lengthy post-dinner-out argument and make-up session that establishes what’s at stake, she laments their lack of forward motion, their teeny New York apartment, while he wheedles her into remembering just how much she really does adore his smilin’ Irish eyes — and oh yes, abs. They yell and march about, and she tosses a few shoes across the narrow expanse of their bedroom (note the shoes — these are Important Later), and then he does a little show that involves his boxers and his abs, and soon they’re proclaiming the depth and foreverness of their coupledom.
Until… the next scene, when he’s dead of a brain tumor and she’s at his wake, held by her meddling mom (Kathy Bates) at the restaurant she runs. Here you meet Holly’s several friends, as they engage in some drinking and weeping, all sad and especially worried about her. Holly puts on a bit of a show herself, as the I-can-cope grieving widow, while coupled friends Sharon (Gina Gershon) and John (James Marsters, reminding you how much you miss Spike) offer standard support and unmarried Denise (Lisa Kudrow) hits on random men at the bar (“Are you single?” “Are you gay?”). Here’s where you also meet Daniel (Connick), awkwardly and seriously crushing on Holly in a wholly inappropriate and strangely inoffensive way. If only, you begin to think, this romance gets under way soon, and Connick can bring his peculiar charms to the proceedings.
But no. Daniel is more or less disappeared from the film at this point, leaving the bulk of the emotional work to Holly, who is definitively not up to it. A real estate broker (whose daytimes apparently made her highly aware of the smallness of her nighttime options), she now stays home and misses Gerry. Her missing takes the form of repeated flashbacks and occasional hallucinations, so Butler gets his star-billable screen time: Gerry plays his guitar (“Do all Irish men sing?” she asks, tenderly; “Only the really well hung ones,” he jokes). Some weeks later, it’s her 30th birthday and Holly’s still moping around the apartment, littered with dirty dishes and half-eaten pizzas, as she doesn’t wash her hair and sings along with Judy Garland on “The Man Who Got Away.” Cue the entrance of the concerned family-and-friends.
At the same time, Holly gets her first dose of the movie’s gimmick, the year’s worth of posthumous letters from Gerry, arranged to arrive every day. He just knew that she wouldn’t have a “plan” for her widowhood (and who would?), and so designs to help her over a series of movie-genic humps: task by task, he sends her off to buy new outfits, sing karaoke, get drunk, and eventually, journey to Wicklow County in Ireland, where she met him when she was a winsome, brightly colored college student. (Though Holly never looks quite college-aged or winsome, this flashback does offer Gerry a chance to show what attracted her in the first place.) She meets his parents, opens more letters, and enjoys a seemingly chance encounter with another Irishman who sings, William (Jeffrey Dean Morgan).
It’s not a little depressing that Holly, seemingly capable if slightly manic before Gerry’s death, is so seemingly unable to function without his from-beyond guidance. While the letters-leading-to-flashbacks device occasions something like an explanation for her devastation (really, he was all the fun in her over-planned, under-improvised life), it also limits her characterization to memories of moments with him. The friends and mom put up with all this, going along with any number of Gerry-arranged outings (including the trip to Ireland), as if they have nothing else to do but attend to Holly’s year of mourning. If she’s not plainly grateful for their infinite patience and energy, you certainly are, as their snarky observations ease the schmaltz on any number of occasions.
Which brings us back to Daniel, who finally reenters the picture just when Holly’s deciding on a new career and looking more forward than back. He offers more clumsy hopes for romance and a few choice moments: “What do you people want?” he wonders about women, feeling forever lost when it comes to pleasing her or other unseen objects of flirtation. Treating her to an “Irish” memorial and corned beef sandwiches, Daniel gives up. Holly apologizes for “bringing up” Gerry yet again. And Daniel looks her in the eye and states what you’ve been thinking for the last hour: “Yeah, I am tired of it.” Thank you, Harry Connick, Jr.