Wednesday, 29 July 2026

Prime Time: Drop Dead Gorgeous (1999)

The argument has been made that 1999 was one of the greatest ever years for movies. I don't know if I buy into that, although it's hard to dismiss any one of the major titles that a movie fan could namecheck for you. It was an undeniably strong year though, and a number of movies created a butterfly effect still reverberating through the cinematic landscape to this day, and may keep affecting things far into the future. Drop Dead Gorgeous, on the other hand, is one 1999 movie that didn't necessarily have that kind of impact. I would argue that it's equally deserving of praise and celebration though.

The debut feature from director Michael Patrick Jann, working from a screenplay by Lona Williams (who also gave us the very enjoyable, and sadly forgotten, Sugar & Spice), Drop Dead Gorgeous is a mockumentary that I would actually rate higher than many of the films directed by Christopher "master of the mockumentary" Guest. It's all about a teen beauty pageant, and allows viewers to follow the determined Amber Atkins (Kirsten Dunst), the seemingly destined Becky Leeman (Denise Richards), the absolutely impartial, honest, pageant host, and mother to Becky, Gladys Leeman (Kirstie Alley), and a number of other wonderful and quirky characters.

As well as those already mentioned, the cast list here includes Ellen Barkin, Allison Janney, Brittany Murphy, Amy Adams, Mindy Sterling, Alexandra Holden, Matt Malloy, Michael McShane, and Will Sasso (if you don't recognise the names then, rest assured, you should recognise the faces). They're all doing great work, and everyone gets such an equal chance to shine that I would find it impossible to single anyone out ahead of anyone else. Dunst, Richards, and Alley feel like the three sides of an important trio though, and they should be happy to have this film on their respecting CVs. Between this and some of her other roles at the time, Richards shows such a knack for slyly comedic material that I am always sad we didn't get her in more features that could have made better use of her talent.

There are some moments of dubious taste, to put it mildly, and one or two words are thrown around casually that wouldn't be thrown around so much nowadays, but there's a consistent effort made to ensure that most of the jokes are targeting the concept of beauty pageants, whether it's mocking the importance bestowed upon them by people who may keep that as an all-time high point in their lives or showing the damage caused by the focus on looks, weight, and generally being viewed as an ornamental object capable of stating vapid platitudes instead of a fully-rounded human being. 

The real test of any mockumentary is just how convincing it is though, how easily can you forget that you're watching something scripted and acted. This is where Drop Dead Gorgeous manages to remain high in my own list of great 1999 movies. I struggle to think of any one moment that strikes a wrong note. Maybe a couple of the gags are just a bit too hilarious to ensure the purity of the format, but I'll happily put up with that if I can continue to cry tears of laughter as Denise Richards presents a very special interpretation of "Can't Take My Eyes Off You".

Every one of the main people involved with this, behind and in front of the camera, has delivered other work in the years since it was released. Some of that other work is great, particularly when you think of the powerhouse performances we've had from Dunst and Janney in the last quarter of a century, but I would still hold this as a very high benchmark for everybody named in the credits. It's still as beautiful as ever.

9/10

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