Goofy ensemble comedy riffs on The Wizard of Oz

Sunny summer flick features several celebrity cameos

Advertisement

Advertise with us

Unabashedly all over the place, this amiable ensemble comedy from director and co-writer David Wain (known for the sketch show The State and the Wet Hot American Summer movies) delivers a nonstop, hit-and-miss stream of dirty puns, slapstick gags and absurdist non sequiturs.

Read this article for free:


or

Already have an account? Log in here »

To continue reading, please subscribe:

Subscribe and receive a limited-edition Free Press branded hat or tote.

Digital Subscription

One year of digital access for only $205*

  • Enjoy unlimited reading on winnipegfreepress.com
  • Read the E-Edition, our digital replica newspaper
  • Access News Break, our award-winning app
  • Play interactive puzzles

*First annual payment billed as $205.00 + GST for one year. This annual subscription will automatically renew at $233.00 + GST every 52 weeks (10% off the regular annual price of $259.35). Offer available to new and qualified returning subscribers only. Cancel any time.

To continue reading, please subscribe:

Add Free Press access to your Brandon Sun subscription for only an additional

$1 for the first 4 weeks*

  • Enjoy unlimited reading on winnipegfreepress.com
  • Read the E-Edition, our digital replica newspaper
  • Access News Break, our award-winning app
  • Play interactive puzzles
Start now

*Your next Brandon Sun subscription payment will increase by $1.00 and you will be charged $17.95 plus GST for four weeks. After four weeks, your payment will increase to $24.95 plus GST every four weeks.

Unabashedly all over the place, this amiable ensemble comedy from director and co-writer David Wain (known for the sketch show The State and the Wet Hot American Summer movies) delivers a nonstop, hit-and-miss stream of dirty puns, slapstick gags and absurdist non sequiturs.

The plucky, self-deprecating cast manages to pull off some good comic moments. And as with the old Zucker-Abrahams-Zucker movies, when a bit doesn’t land, you can just wait 45 seconds or so for the next one.

Still, the film is riffing on The Wizard of Oz (with added sex jokes!). While’s there’s no need to go to David Lynch levels of obsession with this touchstone of Americana, it might help if all the funny stuff added up to something more.

Sony Pictures Classics 
                                In Gail Daughtry and the Celebrity Sex Pass, (from left) John Slattery, Ben Wang, Miles Gutierrez-Riley, Zoey Deutch and Ken Marino are loosely inspired by characters in The Wizard of Oz.

Sony Pictures Classics

In Gail Daughtry and the Celebrity Sex Pass, (from left) John Slattery, Ben Wang, Miles Gutierrez-Riley, Zoey Deutch and Ken Marino are loosely inspired by characters in The Wizard of Oz.

The titular Gail Daughtry (Zoey Deutch) is a peppy, optimistic gal from rural Kansas, best known for penning an essay for her community newspaper titled Why I’m Never Leaving This Town.

A former head cheerleader, she is currently engaged to the former football captain, Tom (Michael Cassidy), and already mapping out their perfect marriage, their perfect home and their three perfect children.

Because Gail Daughtry is meant to parallel The Wizard of Oz’s Dorothy Gale — note the switched-up similarities in the names — her carefully planned life is about to be blown off course by an erotic tornado. She and her fiancé have a casual conversation about a hypothetical “celebrity sex pass” — if either of them encounters their famous crush, they’re allowed to break the monogamy rule — and then Tom immediately runs into his celeb pick. (Look out for a good-sport appearance here by a well-known actress.)

After happening on Tom and his actress mid-sex act, Gail decides the only way to get her universe back in balance is to hook up with her own celebrity crush. Thanks to repeated teenage viewings of Mad Men, this is Mr. Don Draper himself, Jon Hamm.

Soon Gail is off to Los Angeles to see the great and powerful Hamm, along with her best friend Otto (Miles Gutierrez-Riley). (Get your anagram solver out for that character’s name.) The pair encounter Caleb (Ben Wang), an eager but inept assistant at the talent agency CAA; Vincent (longtime Wain collaborator Ken Marino, who also co-scripts), a washed-up People magazine paparazzo; and John Slattery, also of Mad Men fame, playing a scruffy has-been version of himself. (The film claims at one point that Slattery hasn’t worked for over a decade, which would be news to anyone who saw last year’s Nuremberg.)

These three guys are equivalents — kind of — to the Scarecrow, the Tin Man and the Cowardly Lion. Meanwhile, thanks to a mix-up involving identical pieces of luggage at LAX, the gang gets pulled into criminal hijinkery in a What’s Up, Doc?-type subplot, ending up on the wrong side of a (metaphorical) wicked witch (Sabrina Impacciatore) and her hapless flying monkeys (including Joe Lo Truglia).

Sony Pictures Classics 
                                Gail (Deutch, left) and her best friend Otto (Gutierrez-Riley) take a trip to L.A.

Sony Pictures Classics

Gail (Deutch, left) and her best friend Otto (Gutierrez-Riley) take a trip to L.A.

Any brief written summary of all this silliness suggests more structure than the story actually achieves on screen, where we mostly watch the characters noodle around L.A.

There are random encounters with Los Angeles cabbies and concierges and crooks, often played by alums from previous Wain projects (including Richard Kind, Michael Ian Black and Thomas Lennon).

There are also several famous people playing versions of themselves, including a predictably polite and adorable Henry Winkler, a heavily armed and angry (Weird Al) Yankovic and a game Elizabeth Perkins. Paul Rudd drops in for a silent cameo as an ideal wedding guest (because of course).

The film has a flat, cheap, 1990s movie-of-the-week look, and there are slumpy sections where the hit-and-miss ratio skews toward the misses. The Oz references can be cute — keep an eye out for some ruby slippers — but they never seem necessary. Some of the cameos feel gratuitous, as if Wain were on the phone calling up old friends and offering them walk-ons.

Still, there’s a goofy enthusiasm here.

We’ve got Gail’s sunny Midwestern naivety, effortlessly embodied by Deutch, and Hamm’s bubble-wrapped self-involvement, which demonstrates — as many of the actor’s post-Mad Men gigs do — a sly self-awareness about his celebrity image.

Sony Pictures Classics 
                                Jon Hamm plays a version of himself in Gail Daughtry and the Celebrity Sex Pass.

Sony Pictures Classics

Jon Hamm plays a version of himself in Gail Daughtry and the Celebrity Sex Pass.

And while the out-of-towners premise could come off as a clear showdown between the American heartland and the Hollywood elite, Wain and Marino clearly have affection for both sides. More sweet-natured spoof than pointed satire, Gail Daughtry and the Celebrity Sex Pass is an aimless, funny saunter down the yellow brick road.

winnipegfreepress.com/alisongillmor

Alison Gillmor

Alison Gillmor
Writer

Studying at the University of Winnipeg and later Toronto’s York University, Alison Gillmor planned to become an art historian. She ended up catching the journalism bug when she started as visual arts reviewer at the Winnipeg Free Press in 1992.

Our newsroom depends on a growing audience of readers to power our journalism. If you are not a paid reader, please consider becoming a subscriber.

Our newsroom depends on its audience of readers to power our journalism. Thank you for your support.

Report Error Submit a Tip

More Stories

Premier touts Port of Churchill opportunities at Canadian investment summit

Carol Sanders 5 minute read Preview

Premier touts Port of Churchill opportunities at Canadian investment summit

Carol Sanders 5 minute read Updated: Yesterday at 6:58 PM CDT

Premier Wab Kinew announced Monday that major capital investments in the Port of Churchill Plus project will receive an exemption from Manitoba’s seven per cent retail sales tax.

Kinew made the announcement at the start of the two-day Canada investment summit in Toronto. The premier made the pitch to a room of 250 Canadian and global investors representing more than US$13 trillion in assets.

“We are here in Toronto to tell global investors that the Port of Churchill is open and ready to expand,” Kinew told the Canadian Global Growth Forum, a provincial government news release said.

“These new capital incentives make it easier for investors to get in on the ground floor of the largest project featured at the Canada investment summit. The grain and critical minerals we are already shipping out of the port are reaching Europe faster than the Port of Vancouver. With the right investments we can ship commodities year-round, strengthening trade between reliable partners and creating good jobs,” the premier, who was not made available for an interview, said in the release.

Read
Updated: Yesterday at 6:58 PM CDT

Defenceman Morrissey focused on season ahead

Ken Wiebe 8 minute read Preview

Defenceman Morrissey focused on season ahead

Ken Wiebe 8 minute read Yesterday at 12:08 PM CDT

Josh Morrissey insists that a trade request from the franchise goalie doesn’t change his desire to be a lifelong Winnipeg Jet.

The top-pairing defenceman and alternate captain reinforced that view on Monday morning when speaking to a group of reporters prior to the Winnipeg Jets Golf Classic at St. Charles Country Club.

“At the end of the day, I love being here and I love being a Jet. That’s how I’ve always felt,” said Morrissey, who spoke for just over nine minutes on a variety of topics. “That doesn’t change because of somebody else’s decision. Nothing is finalized, so who knows, he could be back. My position doesn’t change.”

Morrissey has two years left on a contract that pays him US$6.25 million and he’s only eligible to sign an extension on July 1, but the future of the franchise pillar will be a topic of discussion as the Jets work to sort through the situation with franchise goaltender Connor Hellebuyck, which remains unresolved.

Read
Yesterday at 12:08 PM CDT

Trade war fuelling spike in city costs

Joyanne Pursaga 4 minute read Preview

Trade war fuelling spike in city costs

Joyanne Pursaga 4 minute read 2:01 AM CDT

A trade war between the U.S. and Canada could cost the City of Winnipeg millions of dollars more than was anticipated during the budget process for this year’s expenditures and beyond.

Read
2:01 AM CDT

Seven years sought for serial harasser

Dean Pritchard 5 minute read Preview

Seven years sought for serial harasser

Dean Pritchard 5 minute read 2:01 AM CDT

Alexander Beaton finished serving a two-year jail sentence for criminally harassing six women and didn’t last two days in the community before he was back at it, sending unwanted obscene messages and videos to a dozen women.

Now prosecutors are seeking a seven-year prison sentence for the 30-year-old Winnipeg man, whose latest string of victims includes a police officer who investigated his earlier crimes.

“He essentially continued (offending) unabated,” Crown attorney Brett Rach told provincial court Judge Malcolm McDonald at a sentencing hearing Friday. “It caused more than a nuisance to these victims — it caused them to fear for their safety.”

Beaton pleaded guilty to 14 charges of criminal harassment, sending indecent communications and breaching court orders for a campaign of harassment waged between 2015 and 2025.

Read
2:01 AM CDT

Treating the disease we simply won’t insure

Rafiq Andani 5 minute read Yesterday at 2:00 AM CDT

There is a condition affecting tens of thousands of Canadians. In 2024, one national measure estimated that almost 120,000 people had the condition. The estimate captures only part of the problem.

Winnipeg venues saying no to AI-made advertisements

Sheldon Birnie 8 minute read Preview

Winnipeg venues saying no to AI-made advertisements

Sheldon Birnie 8 minute read Updated: Yesterday at 10:22 AM CDT

Although the days when telephone poles and notice boards across the city were thick with gig posters, either slopped up with wheat paste or wrapped tight with packing tape, are behind us, the art of making an appealing visual ad for live music events is still a vital part of the local creative scene.

However, a widespread backlash against a new kind of slop — the use of generative AI images — has been building, especially among creatives when it comes to promoting live music.

“Live music is and always has been a DIY type of scene, especially locally,” says Evan Simpson, who has been working as a graphic designer for nearly a decade.

“For years people have been making their own flyers, or if they have the budget, hiring a designer or artist to come up with some artwork for their flyers. It’s a whole ecosystem, a scene supporting itself. If you take away the visual side of it, the spark, individuality and uniqueness of each gig poster is lost. What a sad world it would be if all art were made by AI.”

Read
Updated: Yesterday at 10:22 AM CDT