Cocktail | 1988

For a brief period in 1988, it began to feel like synchronised bartending was the coolest career option available thanks to Roger Donaldson’s cautionary tale of choosing ambition over love.

Brian Flanagan (Tom Cruise), fresh out of the army, arrives in New York, via the inevitable Greyhound bus, with dreams of overnight riches.

There's not an auspicious start as he takes the subway to Vernon-Jackson Station in Queens to hook up with his only contact in the city, Uncle Pat who runs a local Irish pub in Long Island City.

‘Pat’s Place’ was a bar which stood at 10-37 Jackson Avenue on the corner of 50th Avenue. It's now unrecognisable – apart from the distinctive shape – after being spruced up as the hip Jackson's Eatery / Bar.

Despite Pat’s attempt to bring Brian down to earth, the aspiring tycoon has his sights firmly set on a career in Wall Street, or Madison Avenue, or ‘communications’…

He quickly discovers that he’s not remotely experienced enough to step straight into a high-end position and reluctantly settles for tending bar at night while studying during the day.

It’s more Brian’s charm and popularity with female customers than innate ability that get him a job from cynical Aussie Doug Coughlin (Bryan Brown) at the old TGI Friday bar on the East Side.

This stood at 1152 First Avenue at 63rd Street but the candy-striped awnings are long-gone and the premises now houses the Sherlock Holmes-themed Baker Street Pub.

For reasons of economy, the production was based in Toronto and the interior of the popular hangout was recreated in the studio here.

In Ontario too is ‘City College’ where Brian enrolls for a business course, which is Knox College at the University of Toronto.

Coughlin and Flanagan’s bottle juggling routine proves a great hit, oddly taking precedence over speedy service, and the pair are hired to tend bar at “the hottest saloon in town”.

The ‘town’, once again, is Toronto, where 'Cell Block', the blue-lit circular bar in which Brian flagrantly contravenes all manner of health and safety regulations by standing on the bar top to recite poetry, is the Rotunda of the Old Don Jail, 550 Gerrard Street East.

The Don Jail, east of the Don River in Toronto's Riverdale neighbourhood, was built in 1864 as the Toronto Jail, with a capacity of 184 inmates. Before capital punishment was abolished in Canada, Toronto Jail was the site of twenty-six hangings, the last being as recently as 1962.

The Jail was renovated to serve as the administrative wing of Bridgepoint Active Healthcare in 2013, and its Rotunda is open to visitors.

Doug and Brian’s ambitious plans to open their own ‘Cocktails and Dreams’ establishment come to grief after a fist-swinging falling-out over the flirtatious and rich Coral (Gina Gershon).

Giving up on the dull business course, Brian heads to the West Indies for an apparently lucrative gig running a beach bar in Jamaica. The was the Dragon Beach Bar, Dragon Beach in Port Antonio, which went on to find fame under the name of, yes, the Cruise Bar. Sadly, it’s since closed.

You can still enjoy Dragon Beach itself and, a few miles east, you can visit Reach Falls, on the Drivers River, which is where Brian frolics with holidaying New Yorker Jordan Mooney (Elizabeth Shue).

In 2010, Tom Cruise returned to Port Antonio for the tropical island scene in Knight And Day

If you want to boogie the night away in the reggae-filled ‘Dance Cave’, well, that’s back in Toronto. This 'tropical' hideaway was filmed inside Lee’s Palace, 529 Bloor Street West.

Lee’s is also the rock venue where Sex Bob-omb perform in Edgar Wright’s 2010 adaptation of Scott Pilgrim Vs The World.

A bad bet with Doug, who’s turned up on honeymoon with his wealthy new bride, leads Brian to enjoy a fling with the older – but rich, Bonnie (Lisa Banes).

Jordan, understandably humiliated, is on the first plane home, back to her job in a ‘New York’ diner.

Well, sort of. ‘Jerry’s Deli’, where she waits tables – and later gets to dump the day’s specials onto the contrite Brian, is the famous Lakeview Restaurant, 1132 Dundas Street West, Toronto.

This 24-hour eaterie dates back to 1932 and its period deco interior has appeared in Troy Duffy's 1999 The Boondock Saints, the 2007 musical Hairspray, David Cronenberg's 2012 Cosmopolis, with Robert Pattinson, and famously became 'Dixie Doug's', the faux-Southern pie restaurant in Guillermo Del Toro’s Oscar-winning The Shape of Water.

Brian, now living with Bonnie back in New York, realises the terrible mistake he’s made. It’s outside a gallery alongside the old Regency Theatre, which stood at 1987 Broadway at West 68th Street in New York, that he drunkenly breaks up with her.

The Regency, which seems to be showing Casablanca, was indeed a rep house showing classic films. It closed in 1999 and the whole block has been rebuilt.

Jordan is in no mood to take Brian back but, after a wise word from Uncle Pat, he storms off to her family’s luxury apartment on – where else? – 'Park Avenue'.

That expansive lobby, where Brian has to get past the doorman, is actually that of the Canada Life Building, 330 University Avenue at Queen Street, in Toronto’s Downtown core.

Once he gets up to the penthouse to confront Jordan’s father (Laurence Luckinbill), who tries to pay him off with a $10,000 cheque, the elegant blue and white living room is Lady Pellatt’s Suite in Casa Loma, 1 Austin Terrace at Spadina Road, on a bluff overlooking northern Toronto. The Suite has had a slightly warmer makeover than its clinical pale blue-and-white colour scheme in the film.

The mock-Gothic folly of Casa Loma has proved a real boon to the city’s film industry, featuring in countless productions, most famously as Professor Xavier’s Academy in Bryan Singer’s first X-Men movie, but also in Scott Pilgrim Vs The World (again), David Cronenberg's Dead Ringers, Keanu Reeves sci-fi Johnny Mnemonic, and Oscar-winning musical Chicago.

‘Hysteria’, the smart floating nightclub now run by Doug, is The Water Club, in a barge moored on the East River at East 30th Street, in New York's Murray Hill.

Unless you want to hire the club, you've missed your chance for a romantic meal here. From 1982 to 2018, The Water Club operated as a restaurant but it's now used exclusively as a venue for private events.

Things are not going as well as they appear on the surface, and Brian finds himself hit by a dose of reality when he has to attend a funeral, held in St John’s Norway Cemetery, 256 Kingston Road at Woodbine Avenue, in Toronto. Picturesque and conveniently close to film studios, the cemetery has also been seen in Gus Van Sant's 1995 To Die For, John Singleton's Four Brothers, and Jim Sheridan's Get Rich or Die Tryin'.

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