With Run The Series, The A.V. Club examines film franchises, studying how they change and evolve with each new installment.

Before the term “hipster” was co-opted and degraded, the word was just a variation on “hepcat,” referring generally to musicians, comedians… really anyone keenly aware of what’s square and what’s cool. From the end of WWII to the beginning of the LBJ administration, some of the hippest guys and gals were also America’s biggest stars. By the time Beatlemania hit, Frank Sinatra, Dean Martin, Bing Crosby, Bob Hope, and their peers represented the stodgy establishment that the rock ’n’ roll generation was looking to defy. But they weren’t always so creaky. These old-guard entertainers all came up through vaudeville and jazz clubs, where they developed a refined sense of sarcasm and a slick line of patter—much of it picked up from “the boys in the band,” who’d learned it from black entertainers in after-hours joints.

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That particular strain of unflappability flowered fullest in Sinatra and Martin’s “Rat Pack,” who conversed in nudges and inside jokes, and rarely seemed to care if their audience kept up. They peddled coolness to 1950s Las Vegas audiences, and then in a handful of movies and TV specials in the early 1960s. But a decade before all that, Americans got hip via Hope and Crosby’s “Road pictures.” Between 1940 and 1947, the duo starred in five of these Paramount comedies, partly pitched as parodies of various popular globe-hopping adventure genres, and partly as a showcase for a couple of smart-ass radio stars.

In the 1930s, the biggest comedy teams were mostly carryovers from the silent era, mixing verbal wit with costumed slapstick, delivered by broad “types.” But when Hope and Crosby were together, they played themselves, more or less. The character names changed from picture to picture, but they nearly always started out as fast-talking song-and-dance men, who never took even the direst life-or-death situation too seriously.

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The series was a hit from the start, even though the first film—1940’s Road To Singapore—is one of the weakest. For most of their team-ups, Hope and Crosby played horny, savvy underdogs, but here they’re a couple of woman-hating swells, who suffer a string of mishaps that land them on an exotic island, where they’re taken care of by a friendly native. Road To Singapore isn’t as funny or as cleverly self-referential as what would come later; it became a hit largely due to the fast-paced, partially ad-libbed repartee between the two stars, which was unlike anything that movie audiences had heard before. The first film also established some of the Road pictures’ recurring shtick, both good (like the boys’ rivalry for the attention of a shapely, lively young woman played by Dorothy Lamour) and not-so-good (like the stereotype-heavy mockery of other cultures, often delivered by Hope and Crosby in racist makeup and costumes).

The series really started to hit its stride the following year, with Road To Zanzibar. Mid-film, the heroes attempt a stunt they pulled multiple times in Singapore—a version of “pattycake” that ends with them attacking whoever’s threatening them—but when the bad guy ducks, Hope cracks, “He must’ve seen the picture,” winking at the millions of people who saw the first film. That kind of fourth-wall-breaking would become the norm for the Road series, which quickly developed a formula that carried over even into lesser latter-day entries like 1952’s Road To Bali and 1962’s The Road To Hong Kong. In nearly all the movies, fans could expect…

… Crosby to bait Hope.

Although the two actors weren’t locked into types in the way that Laurel & Hardy or Abbott & Costello were, they did fall into the same dynamic over and over in their films. Crosby would be the cool-headed mastermind, who’d come up with a dangerous money-making scheme. Hope would be the hyper chatterbox, who’d let himself get talked into bearing the brunt of any trouble. For their hassle, Hope’s characters usually ended up losing the love interest to Crosby’s characters, along with the bulk of any recovered fortune to Crosby. In the most meta of the Road pictures (and the second-best overall), Road To Utopia, Hope’s Chester Hooton lets Crosby’s Duke Johnson have it, reciting a litany of all the time their schemes went badly for him personally. They finally agree to split up, but as they’re going their separate ways, Duke picks Chester’s pocket, all but forcing him to change course and head up to Alaska.

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… the boys to get into a tight jam that they escape inexplicably.

The Road pictures’ plots were jam-packed, but the screenwriters (which included Melvin Frank, Norman Panama, Don Hartman, and Frank Butler) didn’t pretend they mattered. More than once, the films openly mock the notion that anything that happens has to make sense. In Road To Rio, the entire story hinges on an “important” document, which in the last scene Crosby’s Scat Sweeney reads and tears up, refusing to explain what it says. And in Road To Bali, Hope’s Harold Gridley has an underwater excursion that seems like it’s about to end in his death, but when he makes it to the surface, he chooses to give his explanation in the far back of the frame, out of the audience’s earshot. These movies are full of dodges and red herrings—including, in Rio, a repeated cut back to a galloping cavalry that never arrives.

… the boys to fight over Dorothy Lamour.

When Road To Singapore came out, Hope was third-billed behind Crosby and their leading lady, Dorothy Lamour, who was famous at the time for playing exotic ladies in skimpy costumes. Lamour’s roles in the Road pictures would evolve over the years—with her occasionally even playing somewhat sinister and duplicitous characters—but she was primarily hired to be a rare beauty, and she was often asked to sing and dance in outfits that accentuated her curvy figure. Her heroines also frequently drove a wedge between the heroes, who each took turns trying to romance her. Those woo-pitching scenes are some of the sweetest and funniest in the series. Crosby’s best comes in Zanzibar, where the two of them take a boat ride where they make fun of phony Hollywood love scenes, until they realize that they’re in one. Hope’s best is in Utopia, where Lamour’s scheming character makes insults sound like compliments, until he finally gets so worked up that he turns to the camera and says, “As far as I’m concerned the picture could end right here, folks.”

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… meta-gags galore.

Hope’s nod to the camera during his big love scene isn’t at all off-brand for the series, which was always talking to the audience and putting moments in quotation marks. The meta-gags are especially thick in Road To Utopia, which features a running bit where humorist Robert Benchley pops up in the corner of the screen to explain what’s happening as best as he can, and also includes a moment where Hope is moved by the sight of a mountain that looks like the Paramount logo.

… songs and self-mockery.

Hope and Crosby both emerged from vaudeville, and their movie collaborations were extensions of that tradition, featuring a little patter, a little bawdy humor, and a little music. Frequently, the songs themselves would be big comedy set pieces. Road To Morocco is the best film in the series for a number of reasons—most notably because it was the third in three years, and by the time the team made it they’d become a well-oiled machine. But it’s also a winner because it contains two of the most memorable musical performances. One’s the title song, where the stars predict the plot of the picture, based on what usually happens in these films. And later, while stranded in the desert, the boys experience a shared mirage of Dorothy Lamour, with whom they sing a number where all their voices have been switched around. They take advantage of the mix-up to do their meanest impressions of each other.

… a lot of hep talk.

The original appeal of the Hope/Crosby pairing was the players’ quickness. They were so ready with a quip that audiences barely had a chance to finish laughing at a Crosby line before Hope had topped it (and vice-versa). And when they weren’t making “jokes” per se, they both just talked in humorous way. Even relatively disappointing movies like Road To Bali can be counted on for some snappy dialogue—like when the boys grow bushy beards on a long journey and Crosby notes, “It’ll take a mowing machine to get this hedge knocked off.”

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Very occasionally, the snappy chatter was even put in service of some actual acting. Crosby has a very nice scene in Road To Rio where his Scat tells Lamour’s distraught Lucia Maria De Andrade about his days playing music for Hollywood movies, while the two of them sit in a theater on a cruise ship and watch one of those pictures. Scat urges Lucia not to put too much stock in fantasies, by letting her know what was really happening behind the scenes with the film’s two romantic leads.

Nevertheless, the largely ship-bound, plot-light Rio gave some indication that the series was running out of steam. That may explain why Hope and Crosby took five years off before the next one—during which time Crosby cemented his reputation as an Oscar-caliber actor and pop-music legend, while Hope made some of his best solo comedies, and became a TV star. When the duo re-teamed for the Technicolor Road To Bali (the only Road picture in color), the movie came off as a perfunctory rehash of everything that had worked before. Its best gag involves the boys running into Humphrey Bogart—or rather, African Queen footage of Bogie—and Hope finding the actor’s Oscar and launching into an acceptance speech.

The most fascinating entry in the entire franchise though is also the worst—and the last. From the inexplicably superfluous “The” to the most excessive use of ethnic stereotyping since Singapore, The Road To Hong Kong is a weird case of a venerable property awkwardly trying to contemporize while clinging to the wrong old-fashioned elements. Hong Kong relegates an aging (but still plenty va-voom) Dorothy Lamour to a cameo appearance, while Joan Collins steps in as the love interest. Meanwhile, the boys get embroiled in a spy caper that sees them dealing with villains straight out of a James Bond novel (a few months before the movie version of Dr. No came out), and getting shot into outer space as a last-minute replacement for apes. Through all the up-to-date hijinks, Hope and Crosby found time to crack jokes about Hong Kong’s “bamboo television antennas,” to sing a song that’s a litany of Asian clichés, and to do wacky Chinese accents.

The stars didn’t do themselves any favors by including a cameo by Peter Sellers, who at the time was building a reputation as one of Britain’s brightest comic actors. In a way, the Sellers scene is as clunky and questionable as the rest of The Road To Hong Kong. He does one of his brownface routines, playing an absent-minded Indian doctor. Still, Hope and Crosby let their guest upstage them—very unusual for the series—and for a few minutes the sense of absurdity changes the entire energy of the film. For rock ’n’ roll era moviegoers, a semi-surreal line like Sellers’ “you are suffering from a severe attack of teeth… and two cavities” came off as much weirder—and thus cooler—than shots of Hope and Crosby waddling around in spacesuits designed for monkeys.

And yet, again, there are times here when the duo recaptures their old magic. When Hope’s Chester Babcock needs a piece of paper and Crosby’s Harry Turner asks, “Got a racing form or a summons on you?”… that’s the old stuff, right there. And while The Road To Hong Kong isn’t so great compared to what came before, it’s really the last good starring role for Hope, who spent the rest of the 1960s making the likes of Boy, Did I Get A Wrong Number! and How To Commit Marriage. Crosby, meanwhile, joined the ensembles for Robin And The 7 Hoods (alongside the Rat Pack) and the 1966 remake of Stagecoach, then more or less quit the movie business. The end of the Roads came right as something else was about to begin—a year or so before The Beatles would hit it big with a public persona that relied a lot on zippy give-and-take, like a supercharged Hope and Crosby. And so the cycle rolled on. Any time a comedian or musician winks at the camera or pretends to be too cool for the room, the Hope and Crosby estates should get a nickel.

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Final ranking:

1. Road To Morocco (1942)

2. Road To Utopia (1946)

3. Road To Zanzibar (1941)

4. Road To Rio (1947)

5. Road To Singapore (1940)

6. Road To Bali (1952)

7. The Road To Hong Kong (1962)

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