Alan Cumming did not receive an Oscar nomination for portraying Wyatt Frame in Josie and the Pussycats.
Why that is actually isn't some great mystery, as it basically takes the same overall approach as Scooby-Doo, which is to be both a sendup of the old while also still being the old. The difference is just that the jokes are better and so are the performances. To the point I do question what this film did to the critics who watched as it presents itself as silly fun, is silly fun, what more did they want? Anyway, the element that most realizes this fundamental fun is Alan Cumming, who is always a bit of a broad actor which is ideal for the over the top tone featured in this film. As we open with the presentation of a boy band that is every boy band of the period wrapped together as one and dictated terms by Cumming's Wyatt. Cumming's whole performance is going hard into a purposeful stereotype of the over the top English agent, with such an accent and just overt mannerisms in every choice. Choices that wholly work in this first scene where he's that, while also playing it as though he is a teacher handling some rowdy students as the band argue with one another. Cumming's directions to them being perfectly timed for some comedic gold, particularly his change to an extra stern voice when it seems like one of the band members might continue a conflict. Cumming easily accentuating each little bit of business in this opening. Something that immediately changes when the band asks about something weird in their album, to which Cumming's expression changes from exasperation of wrangling talent to overt evilness in his eyes as he immediately sets up the intended death for the band and literally parachutes off to find a new act to exploit.
That brings us to the titular Josie (Rachel Leigh Cook) and the pussycats Valerie (Rosario Dawson) and Melody (Tara Reid), whom Wyatt doesn't find for their talent, just his ability to use them as he sees fit. Where Cumming again takes on the over the top agent demeanor as he offers them fame and fortune as though he is indeed narrating about fame and fortune himself. Cumming wonderfully plays around in the scenes with the knowing quality that his character is essentially this supervillain planning on putting them into a Faustian deal. Cumming riffs on the scenes brilliantly by often just accentuation of lines such as explaining why the band need to single out Josie, or whenever they question his swift dismissiveness of them consistently. My favorite bits though are his glances one way or another whenever he is directly alluding to his evil intentions whether that being a knowing glance one way, or just adding the right degree of sinister glee behind a certain line that speaks more so to the truth of his evil. Cumming playfully knows precisely what he is doing at every turn in just finding the hilarity in each bit. He's having the right kind of fun with it as being two types of over the top, villain and agent, and just running with it for some consistent comic gems every time he has pithy one liner delivered with venomous intention or swift side eye denoting his ever scheming nature.
Cumming delivers a performance that I could just run down every moment to find something enjoyable there, but I'll limit to a few favorites. One where the band comments on former haters loving them now, and Cumming starting with the same phony reassurance that it is just a great part of being famous before noting getting back at one's high school peers usually requires ten year reunions, where Cumming's moment of looking inward for a moment, reliving some personal trauma in his silence for a moment before regaining his composure with a smile is absolutely hilarious. Another such bit when he, and co-conspirator head of the record company Fiona (Parker Posey) both laugh together in their evil scheme, and the two talented actors purposefully chew scenery together in trading their over the top maniacal laughs, and it is pretty glorious. My favorite bit however is when he's trying to isolate Josie from her potential boyfriend, and the other band mates, and to get her to listen to a brainwashing cd to turn her into an egomaniac. Cumming's great in his labored delivery of every lie to set-up that Josie's Alan M. isn't interested, before each time making a phone call to set up the line, with the most obvious immediate call each time, that again Cumming couldn't be more obvious in doing and couldn't be better. Highlighted though by his haughty phony anger when wagging his finger at Josie to cover up his obvious scheming. I'll even give credit to Cumming, and Posey by extension in their selling of a final bit where both villains reveal themselves to be old high school outcasts, a bit that on the whole didn't entirely work for me, but even then I enjoyed Cumming's one last change in his demeanor to suddenly have a extremely insecure American accent and a rather silly hangdog expression. One last bit however that exemplifies the entirety of his work, that knows exactly what film he's in and sells it to its fullest.
