This Is Spın̈al Tap (1984)

It is extraordinarily rare for a director to change the entire direction of comedy with their first feature, but that’s exactly what Rob Reiner did with this legendary mockumentary. Following a disastrous American tour by a witless British rock group, This Is Spın̈al Tap manages to nail so many music industry cliches so perfectly that the film quickly became a mainstay of tour buses around the world. Reiner himself got in on the act, playing the blowhard documentary director Marty Di Bergi. The fact that something entirely improvised could create so many deathless lines is even more astounding. This year a sequel, The End Continues, was released. What fitting bookends to a brilliant career.

When Harry Met Sally (1989)

Reiner’s run between 1984 and 1992 is the sort of thing most directors can only dream of. He spent those years dabbling in multiple genres, and producing a classic each and every time. When Harry Met Sally is a classic example. It was just Reiner’s second romcom, but it instantly became the defining romcom of all time. Billy Crystal and Meg Ryan play characters who spend years circling one another, unsure of whether a man and a woman can ever truly be friends. The performances are tremendous, the outfits are great, Nora Ephron’s script is perfect, and the emotions never feel anything but completely real. One of the best films ever made, but maybe not even Reiner’s best film.

The Princess Bride (1987)

Here is where Reiner’s approach to film-making started to become clear. This was a man less interested in flashy visuals or personal style, and more interested in finding the best writers on Earth and wringing every last drop of potential out of them. In the case of The Princess Bride, that writer was William Goldman, who crafted a kaleidoscopic fantasy world full of heroism, revenge, romance and magic. Every character stands out. Every line sings. And Reiner gives the material exactly the treatment it deserves, knowing precisely when to hold back and when to gun for the laugh. The Princess Bride is nearly 40 years old, and it remains one of the most impressive family films of all time.

A Few Good Men (1992)

And then Reiner left comedy altogether, to make Aaron Sorkin’s tight, muscular legal drama. Written on napkins during Sorkin’s shifts as a barman, A Few Good Men was first a play that ran for almost 500 performances. But Reiner and Sorkin (and an uncredited William Goldman) spent months reworking the script for the movie adaptation. The effort shows. The story of a callow lawyer working the case of some extrajudicial military deaths, the film quickly becomes a treatise on the battle between duty and morality. The “I want the truth” showdown between Tom Cruise and Jack Nicholson remains the highest point of both actors’ careers.

Misery (1990)

Some might have picked Stand by Me to round out a list like this, or maybe The American President. Maybe even, since his film was the thing that brought the term into common usage, The Bucket List. However, you could argue that no film captured Reiner’s absolute mastery of tone like 1990’s Misery. On the surface it’s a horror film, about a writer who finds himself trapped in the home of an obsessive fan. But it also manages to be screamingly funny, clearly the work of writers (Stephen King and William Goldman) who enjoy a complicated relationship with the consumers of their work. Tense, gruesome and containing one of Hollywood’s all-time great red herrings, this one might just be Reiner’s masterpiece.