Wrote this just a short while ago, though I've edited and improved it to try more clearly (but still long-winded) covey my argument, when we had this same topic (and same concesus) why I think GTA Vice City's songs, even isolated from the broader music (such as original scores) and sound, are great but surpassed by GTA V.
GTA V likely as an overall score, though I need to explain why the scoring of the game is relevant to the soundtrack.
V is the first GTA with an original score. The 80s synth/cyberpunk-esque and jazzy score pieces to the mission set-ups, preparations, and executions are very well crafted and one of the most ambient scores in any game. There are moments where it feels like the cast is in a cyberpunk cityscape, noire thriller, or Michael Mann scene. The work that
Tangerine Dream did on the
action tracks and
The Alchemist did on the
ambient set pieces is masterful. And their skill set is precisely when the soundtrack of GTA V is elevated above other GTA's.
Vice City has an incredibly purposeful soundtrack, and by far the tightest and strongest mood and theme. And it has a track listing that easily compares to GTA V. But what GTA V has that VC does not is that GTA V scores the soundtrack to the story more because Rockstar added a talented team of folks like Tangerine Dream and The Alchemist to do so and produce an additional original score.
Lazlow chose the soundtrack list for both Vice City and GTA V, and I think both fit their rightful themes perfectly. I'd argue almost every GTA's soundtrack is top notch, and Lazlow always seems to find the perfect mix of known and unknown tracks that capture both nostalgia and surprise. In particular, VC stands out because VC is tighter where as GTA V has to have tracks that fit a much wider variety of locales, such as Vinewood, Los Santos, East LS, Sandy Shores, Chumash, and Blaine County, and in that regard GTA V has a soundtrack that fits 5 or 6 themes very well opposed to VC needing only 1 theme. And in that regard, both soundtracks fit their respective moods well, and are loaded with gems. Worldwide FM and FlyLo FM deserve special note for just finding free roaming gems, but this is more subjective. Objectively, the thematic choices for the varied geography of GTAV are complimented very well by Los Santos Rock Radio, Mirror Park, The Lowdown, and Rebel Radio, and East Los FM much in the same way that Emotion, Fever, Flash, and VRock perfectly complimented VC.
But what sets GTA V above is that it also has its own masterful original score created by a very talented team, and that team was able to better utilize the soundtrack. VC's likely most iconic moment utilizing the soundtrack is only Flock of Seagulls, but GTA V story has numerous moments utilizing everything from Seger, Chicago, NWA, Green Velvet and Harvard Bass, Smokey Robinson, and T.S.O.L. The scoring of the story, precisely because it had the team doing the original score to the story and missions, also better utilized its soundtrack for key moments in the game.
Arguing about the best colour or taste is a little silly of course but objectively speaking GTA V had by far the best musical production of any GTA game. It's the only GTA with an original score and the only GTA that makes tailored use of its soundtrack for in-game moments. Even the trailers, the best in the series, have made The Chaingang of 1979's Sleepwalking icon for GTA V, but that's much in the same way Vice City was even more iconic for Flock of Seagulls. It's the in-game use, however, that sets GTA V above GTA VC. Sometimes it just changes your radio station, such as Trevor Philips Industries beginning with Soulwax FM in the car. But often, a specific song has been chosen to set the mood of a mission. The game has a lot of great moments that are in part defined precisely because it picks specific songs to play on the radio at that time, such as NWA's Appetite for Destruction for Franklin & Lamar, Waylon Jenning's I Aint Long Living Like This at the end of Mr. Philips, Doobie Brother's What A Fool Believes and TSOL Abolish Goverment-Silent Majority for Crystal Maze, Chicago's If You Leave Me Now finishing Monkey Business, and Black Strobe's Boogie in Zero Gravity for the Jewelry Store. The latter, for example, being the iconic song for completion of all Heist 1 parts and also part of the reason the finale of Heist 1 is one of the best moments in the game.
I think a lot of folks miss that, along with a lot of the world detail and game world life, for that matter, if you only play the game once because you assume it's random and not handcrafted.
I would agree that a good case for either VC or GTAV could be made for having the more purposeful, thematic, and successful soundtrack. VC is probably the tighter and more thematic soundtrack. But I would say as a broader soundtrack listing, and also '
use' of those songs in-game in specific missions and cutscenes, was superior in GTA V. Subjective prefer and taste aside, I think the technical production of choosing and use songs was more competent, active, and purposeful. Overall I would give over GTA VC the edge to GTAV because its soundtrack was more utilized to score the story.