Twisted Metal 4 is easily my most played in the series and the only one I really grew up with. I've also played a lot of Black and adore it, despite it's... often obscene difficulty.
That said, apparently the creators have said they think Black's difficulty is objectively a flaw that holds the game back. Twisted Metal 4 is also, apparently, one of the blacksheeps of the series... the other being TM3. I've played a decent amount of TM3 and I'd have to agree it's pretty rough, but I think TM4's only real crime is feeling out of place with the rest of the series. I mean... it has a damn alien in it.
Also,
@Mr. Daddy is going to want to see this thread.
Yeah so, as he said... I absolutely love Twisted Metal. I started with 3, which, since it as the only one I had played, didn't seem all that bad to me until I had played a bunch of the others years later. Head-On is easily my favorite in the series. I largely think it just does everything the series does well the best of any game in the series with very few exceptions, those exceptions mostly being the handful of new drivers to classic cars being a pretty mixed bag of quality and the final boss just not being great. Outside of that though, Head-On, especially the PS2 port that has way more extra features, is just an overall really strong entry that just feels great to play.
Unfortunately I've never really cared much for TM1. Like, it's alright, but a good chunk of the maps are pretty samey or basic, and if you have a car with anything less than above average handling it probably feels awful to control. Combine that with questionable decisions like bystanders that can actually hurt your car and funky interactions with hitboxes and how ramming damage is calculated and you just end up with an ultimately still fun, but very jank experience.
2 might be my second favorite of the series, but it's hard for me to pick between it and Small Brawl. I mostly find 2 to have the overall best mechanics of the ps1 titles, though it does still inherit a little bit of that TM1 jank, but not much. Mostly just ram damage related stuff. Outside of maybe Head-On and Black, I also think 2 has overall the best general feeling and vibe with its world, and it easily has a lot of the best versions of different drivers and their endings for me. If it wasn't for the fact that I feel like I could say all the same things about Head-On for the most part and Head-On having generally better mechanics, it'd probably be my favorite. Small Brawl on the other hand is just really charming to me. I've always been a sucker for the "shrunken down/small POV" trope in games, and this game takes that and runs with it. I also always wanted to take actual RC cars and do a Twisted Metal match with them on a playground, and this is literally a game that opens with that, so it kinda just instantly clicked with me. Some of the endings are certainly a little too lacking in that Twisted Metal kind of feel, and at times it's a little cartoonier than I'd normally like for a game in the series, but generally speaking I think it actually keeps the same feel of the rest of the series while being aimed at a bit of a younger audience. I also love the levels in this game in particular, and how interactive a lot of them are. I could say the same about 2, Head-On, and Black in particular, but in general this game does that pretty well. Most of the rest of the games have like a handful of things you can directly interact with, with most of them being destructibles, but Small Brawl just packs them in like crazy and makes them more generally unique, like in the kitchen level you get a can opener that can damage you, a microwave that has a health pickup in it but can be closed to injure anyone inside, a refrigerator that has an ice environmental attack, a stove that can burn anyone that runs over a hot coil, a plumber that you can launch napalm at to make him fart and destroy the underside of the island in the middle of the kitchen which is also the secret to unlock Darkside, mousetraps that launch you to the top of the kitchen island in the middle of the map, and a handful of different destructibles that may or may not hide pickups, like the plumber's toolbox. Just overall a really strong entry.
3 has generally dropped to being my least liked entry in the series. I don't really have much positives to really say about it... Outside of some endings that I like, and a few maps that I think are pretty solid, it's just kinda bad. Mechanically it somehow feels worse than 2, the AI is just way too aggressive to really work with, a lot of the maps are full of annoying hazards, so many of the characters are misunderstood (Sweet Tooth, a grown adult who owns an ice cream truck and who is an insane clown who doesn't give a damn about stealing or killing people over trivial bullshit, wants... the ability to eat all the candy and ice cream he wants? Which he could totally already do??) or just get kinda bastardized (Axel, who wants nothing more than to be separated from his machine, now wants to... become one with it?). It just feels really confused, and I know that behind the scenes a lot of the issues are kind of explained by the fact that it and 4 weren't developed entirely by the same team (the 989 studios team did have some hand in 1 and 2, but not so much from a creative standpoint), but it still doesn't really help.
I have much more... complicated feelings on TM4. I actually think the levels and mechanics of this game are really strong. It kinda feels a lot like TM1, but generally more polished and good feeling. I like a lot of the concepts used, like custom cars, and some of the character ideas. Some things I think are a little more complicated, like having a boss at the end of each level. On the one hand, I do think it's neat and overall adds to each level, but also just makes the game feel and take longer than it really needs to, and with how large some of the levels are, it can actually make a lot of the bosses take even longer because a lot of them get kind of lost trying to find you. I also... really don't like a lot of the newcomers. I think it often steps over the line of that feel from a dark and twisted world with only a small hint of the fantastical to just being a weird and wacky cartoon with a small hint of that dark and twisted tone. I also particularly am not fond of the fact that the custom cars and all of the bosses, even the ones that are just returning characters, don't really have an ending. Probably the biggest mixed bag from the series for me.
Black is also up there among the peak of the series for me, despite its often unnecesary difficulty. This game actually scared me when I first got it as a kid because when I first played it, I was pretty sensitive to gore, and I saw Yellowjacket's driver profile and freaked out, lol. A lot of what I like about the rest of the series though is still present here, especially really solid level design. I also absolutely love that the team just did everything they could to make the game as dark as possible, though admittedly I do wish we could have gotten the Preacher scene that got cut. Not much to say about it that I haven't to some degree already said about the other games I like in the series.
PS3 is like 4 for me in the sense that, while overall I like it, my feelings are complicated. Mechanically, I think it's one of the best in the series, possibly even the best in the series. It just feels great, and a lot of the levels are awesome and have a lot to them, and I love the concept of some of the levels being just smaller sections of larger levels. The new story mode is also pretty neat, and some of the new gamemodes are also really fun. The bosses are a bit more of a mixed bag, though. Probably a little more complex and high concept than I'd really want, especially the second boss. Some of the new vehicles also are kind of hard for me to really make my mind up on. Like, adding a helicopter is a neat idea to me on one hand, but also at the same time, I can't help but feel like as an actual vehicle it... kinda just sucks. It's got like no armor, has a hard time healing, the AI just kinda always know where you are so you can die way faster than you mean to, and against people while you can certainly get the drop on them it still pretty much has the same problem. Similarly, Juggernaut, the truck with a trailer that has bombs in it, is a neat idea, but does way too much ram damage to other cars... and itself. It's also borderline unusable on certain maps, and just feels way too strong at times and pathetically weak at others. Also kinda hate that Axel was made as a pre-order bonus exclusively, until they made him available in an update like right before they took the game's servers down. I'm also really not fond of there only being four drivers, and having drivers separated from their vehicles. It just feels so wrong for Needles to be driving Crimson Fury. And I just kinda feel robbed that certain newcomer vehicles like Meat Wagon or Kamikaze just won't have their own drivers associated with them unless they return in another game later. That said, the characters that are here have pretty good stories, and I was happy to see a Black style return to cutscenes, with a beginning, middle, and ending scene.
Oh, I uh... I'm close to the character limit. I guess my main takeaway, or if you just don't wanna read my loving rambling: Play Head-On, 2, Small Brawl, and/or Black, they're fantastic. 4 and PS3 still have plenty of good reason to play them and are overall solid mixed bags. You could probably skip 1 and 3 without missing too much.