Loverboy (1989)

A 1989 romantic comedy about a pizza delivery guy whose female customers keep falling in love with him, and the loneliness at the center of the joke. The film is honest about what the women are lonely about, and the honesty is the part most 80s comedies of this kind were not willing to risk.

What the film does

Patrick Dempsey plays Randy Bodek, a Princeton grad with a philosophy degree who cannot find a job in his field, takes a pizza delivery job in a beach town, and discovers that the women on his route keep inviting him in. The film is a series of set-pieces in the women’s homes, each set-piece a different woman, each woman a different kind of lonely. The film is not punching down at the women. The film is asking what a young woman’s apartment looks like when nobody is in it, and the film takes the question seriously.

Kate Jackson plays Alex, the one real relationship of the film, a single mother with a teenage son and a job she does not love, who orders pizza so she can have an adult in the house for ten minutes. The relationship that builds between Randy and Alex is the heart of the film, and the film is the rare 80s comedy that lets the romantic relationship be the main event instead of a subplot. The film is also the rare 80s comedy directed by a woman. The two are not unrelated. The film looks at the women in the apartments the way a director who had been a woman in an apartment would look at them.

The third act is the comeuppance, and the comeuppance is real. Randy gets caught, the women he has been visiting confront him, the film does not flinch. The film is not interested in Randy being forgiven. The film is interested in Randy understanding what he was part of, and the film takes the time to let the understanding happen. The third act is short and is the best part of the film.

Why it’s in the canon

Criteria blend is 1+3, loved it and want to remember it. A fun 80s comedy that does not date the way most 80s comedies date, because the fun is in the watching and not in the era of the watching. The film is from 1989 and the film knows it is from 1989 and the film does not lean on the year. The film would work in 1995 or 2005 or 2025. The film’s loneliness is not era-specific loneliness, it is mid-career mid-life loneliness, and that is portable.

The Patrick Dempsey tie to Can’t Buy Me Love is not an accident. Dempsey in 1987 played a high-school kid, and Dempsey in 1989 plays a Princeton grad with a philosophy degree and a pizza-delivery job, and the two performances are recognizably the same person. The film is the same register too, the bright 80s register, the moral register where the bad behavior is acknowledged and the consequence is real. The two films belong in the same canon for the same reason. Both films are about a young man who learns something about himself by being wrong, and the film lets the audience see him learn.

A note on the year

The film is 1989. Letterboxd lists it as 1989. The Wikipedia article is the 1989 film. We use 1989.

A note on disambiguation

This is the 1989 Joan Micklin Silver film starring Patrick Dempsey and Kate Jackson. There is no other feature film of this title in the same year. There is a 2015 film called Loverboy unrelated to this one (the same name, a different film).

On hand

Yes, DVD + digital. The DVD is the Tri-Star release. The digital copy is the same transfer, no extras.