I've now seen both of them.
The 2009 TV Special is structured like the annual Lupin III TV Specials while the 2013 Theatrical Film is structured like the annual Detective Conan movies, and that overall makes it better. Lupin III's cast are inherently travelers and pretty fundamentally flexible in the kinds of stories you can tell with them and so I feel any Crossover with Lupin III will always work better if it's more throwing them into the other franchise's world.
In fact some fans think the biggest problem with most Lupin movies and TV specials is how they kinda follow the same formula, chiefly the Castle of Cagilostro formula.
Meanwhile Detective Conan is a surprisingly rigid franchise for something that has gone on this long and most content produced is technically filler. So even in the movie the Detective Conan characters feel off sometimes. For me personally the movie served as a fun introduction to Detective Conan going into it as a Lupin fan, but once I re-watched it as a seasoned Conan fan how the characters were off became more noticeable.
The Special is still sometimes enjoyable however, but it certainly feels off to watch a Crossover story and find the most compelling part to be the completely original characters. Christina Vee does a great job as Ran's Princess Doppelganger.
Basically Detective Conan is not a franchise that lends itself well to crossovers, even it's connections to other franchises from the same creator are often questionable to the few actually versed in both lores.
Lupin The Third however is tailor made for Crossover potential and it's a shame it doesn't happen more often. In the late 2010s DC Animation gave us a Batman meets Scooby Doo movie and a Batman meets the Teenage Mutant Ninja Turtles movie. I got the impression these kinds of crossover movies for Batman with not even DC stuff would become a regular thing, but it wound up being just those two. I already commented on the Lupin III influence in Catwoman: Hunted, so since people at DC see the relation why not try and actually make a Lupin III meets Batman movie?
Scooby Doo seems to do crossover stuff more regularly, and given how many of their bad guys plans are kind of heists it too could suit a Lupin The Third Crossover well.
But chances are doing it with another Japan based franchise will always be easier to arrange. What other Anime franchises are basically in the contemporary real world and are reasonably Episodic with pulp inspired elements? That's actually a rarer combination then you'd at first expect. Maybe Sailor Moon could work?
The Detective Conan Crossovers happened because they're both TMS, there really doesn't seem to be a third TMS franchise on their level. But TMS is under the TOHO umbrella which opens the possibility of Godzilla.
Update: So the Lupin III project for 2023 is going to be Lupin III vs Cat's Eye an Anime about Classy Cat Burglars from the early 80s, which is a natural crossover choice. But the image we have implies it'll be a return of Pink Jacket Lupin which is interesting.
That makes me think again about the prospect of Lupin III crossing over with Batman, as both Lupin and Batman have had different tones over the years.
The Pink Jacket Incarnation of Lupin The Third is who I'd have show up in Batman The Brave and The Bold the same animated version of Batman used for the Scooby Doo crossover I mentioned above.
I'd have Red Jacket Crossover with the DCAU/Timmverse Batman voiced by Kevin Conroy and other still working BTAS veterans.
Green Jacket I'd have crossover with the Batman of The New Frontier Animated film as a late 60s/early70s period piece, preferably written and directed and drawn by the same staff as The Woman Called Fujiko Mine.
And Blue Jacket (Parts 4 and 5) with the up coming Caped Crusader show or the Tomorrow verse films being the most modern incarnations.
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