[4.4/10] I do my best not to hold a lack of novelty against older works. Yesterday’s ambitious new development becomes tomorrow’s bog standard inclusion. That’s not a reason to slate the original work for no longer having the shine of something new and unexpected.

But good lord, this episode is boring. Most of its electricity is supposed to come from the advent of the holodeck, a device that (with an apparent upgrade) could recreate entire worlds, real or fictional, within the confines of a starship and its “finite space.’ Picard spends much of the episode marveling at the invention, and the script takes plenty of time to have characters explain how it works and note its limitations.

That makes total sense for the first Star Trek episode to use the holodeck in earnest. A little-seen episode of The Animated Series toyed around with a similar idea (with similar problems), and we witnessed Tasha using it for sparring practice in “Code of Honor”. But this is the first full realization of the holodeck as a place to set whole stories and imagine new worlds to inhabit for recreation and adventure.

The problem is that in the ensuing decades, the holodeck itself has become old hat among Star Trek fans, and the dreaded holodeck malfunction has become an amusing trope. Futurama memorably poked great fun at it, adding that the last time the holodeck malfunctioned, the Kirk analogue was “slapped with three paternity suits” -- something that resonates here as Riker’s eyebrows raise when he hears his captain describe how “real” kissing women felt in the holodeck. It’s not “The Big Goodbye”’s fault that the episode relies, in large part, on the advent of this new development that, to later viewers, is anything but new.

What is “The Big Goodbye”’s fault, however, is the dull story it crafts for Captain Picard’s first Dixon Hill adventure. I enjoy a good noir story, and a period setting, and even fish-out-of-water humor, but TNG does none of those well here. The tale itself isn’t terribly interesting, with the show vaguely riffing on The Maltese Falcon among other gumshoe stories. There’s a standard damsel in distress, the usual good cop/bad cop deal, and a few gruff gangsters with nothing to make them stand out or any twist to the tropes. I can see why the Next Generation staff would want to do an old-timey gangster episode -- The Original Series had a blast with it in “A Piece of the Action” -- but they failed to come up with a compelling story worthy of utilizing the setting.

The only compelling wrinkle to this whole deal is the mildly subtle parallel between Picard’s adventures on the holodeck as a fictional character and his real life duties as Captain on the Enterprise. Picard is engaging in this recreation as a mental break from preparing to greet a delegation of aliens who are particular sticklers about etiquette and manners, with the threat of disaster and retribution if it doesn’t go well. That aligns with Dixon Hill having to deal with Redstone, a hard-edged local mob boss who nevertheless puts a premium on etiquette. There’s something mildly clever in the setup, but the episode doesn’t really do anything with it, beyond the faintest intimation that after having dealt with 1940s gangsters, uptight insectoids are nothing.

The other wrinkle, of course, is that the insectoids’ scan of the Enterprise messes up the holodecks safety controls, to where this gumshoe escapade is no longer just fun and games, but a place where people can get hurt. That includes a random redshirt who gets shot in the gut by one of Redblock’s goons. That development at least creates some minor stakes here (though you knew the random, never-before-mentioned crewmember wasn’t long for this world), but doesn't arrive until too late in the episode to give it the shot in the arm it needs (no pun intended). Instead, we mostly just spin our wheels for the first two-thirds of this thing.

The solution inside the holodeck is mildly clever, as Picard has to convince his holographic attackers that great riches await them aboard the Enterprise, causing them to walk out and disappear (albeit, curiously, not as instantaneously as in later episodes). But Picard seems to have very little urgency about his dying crewman or his diplomatic needs, taking time to have a noir-ish conversation with his fictional good cop buddy. And the solution outside the holodeck is just another “Wesley Crusher: Boy Genius” quick fix that isn’t really earned.

Some of that might play better if the episode had more style or were funnier. Despite the fact that this theoretically a noir tale, “The Big Goodbye” doesn’t use many of the trappings of film noir in its presentation. There’s a shot at the end with the slat-blocked light reflecting on Picard and his cop friend that shows some mild imagination, but otherwise, director Rob Bowman stages this one like any old episode, with little in the way of interesting lighting or framing choices to heighten the mood.

The episode also struggles to generate any laughs. Most of the humor is founded on our heroes not being familiar with 20th century customs. Dr. Crusher can’t use a compact mirror! Picard coughs when smoking a cigarette! Data doesn’t understand how plug-in lamps work! It’s basically the same joke over and over, and it never really gets funny. There’s a few moments where the show teases the attraction between the captain and the doctor, but even that devolves into hacky bits about other crew members interrupting their potentially romantic rendezvous. There’s elements like a stylized presentation or better jokes that could have livened this one up, but as is, it’s a dull outing.

Ideally, the audience in 1988 would be in the same mental space Picard is: wowed by the prospect of this new technology, afraid for he and his colleagues’ safety when things go awry, and impressed at his smarts for using the holodeck’s limitations against his unreal adversaries. But for fans as steeped in holodeck stories as Picard himself was in old pulp detective novels, “The Big Goodbye” is only notable as a fumbling first attempt at the genre.

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