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First, let me say, I love adventure games. I've played all of the old school popular games all the way back to Sierra's KQ1. I enjoy all of those, even with the cheap deaths and illogical puzzles. This game though, Jack Orlando, is absolutely the worst adventure game I've ever played.
Story/Presentation: The story is rather silly and that's the biggest part of an adventure game. What really hinders it though is the fact that the dialogue is absolutely horrific. Easily some of the worst voice acting I've ever heard. Plus the dialogue itself is just complete garbage. I turned on subtitles so I could read what they were saying instead of waiting to listen to the voices and seriously, it's like this thing was written by a five year old. This is no exaggeration. Normally I can handle bad voice acting and dialogue, but it really really ruins the game and brings it down a whole level.
Graphics: The graphics are decent at best. Though considering the game was made in the late 90s, there are other games from the same time that blow this game out of the water graphically. The game talks about having a bunch of high class artists draw all the backgrounds and everything, but I have to say, it looks more like something a child would do for art class.
Sound: The music is alright. I tend not to notice music in games for the most part unless it's really annoying. It didn't stand out to me, so it's passable.
Gameplay: Seriously flawed and poorly designed gameplay. It really is like this thing was developed by five years old kids. There are tons of items you can pick up in every screen, but literally 90% of them are useless. They even make a point of that in the manual. That is not good game design. When you do pick something up you can't examine it so sometimes you don't even know exactly what it is. Ridiculous. Then the puzzles are often completely illogical. So it all compounds on top of one another to create just terrible gameplay. On top of that there are tons and tons of locations, many of which I'd say are totally unnecessary. It's like they did it to pad the length of the game. And yes, as others have said you enter an old tomb at one point such as in Broken Sword, but it makes no sense in the context of this game. They don't even explain it. Absolutely ridiculous.
Oh, and yes they have deaths in this game. Something the good developers learned to do away with by the time this game was released. While I can handle dying in a game, it's really poor design when after you die you are forced to reload a save. I didn't realize I was entering a timed and dangerous situation at one point and hadn't saved for a decent amount of time. Died and stopped playing because I didn't want to go through all of the crap again. Apparently the concept of retrying such scenes didn't occur to the developers. Pathetic.
And overall that is what I'd have to say about this game. It's really a pathetic attempt and easily one of, if not the, worst offering on GOG. This is by no means in any way a good adventure game. It's more a compilation of all the terrible ideas from the early days of adventure games wrapped up with a terrible story, horrific voice acting and dialogue, and boring art. Definitely give this game a pass if you can. This is a game I would totally return if GOG allowed it.
this game was like roleplaying a trash digging bum. on the plus side the music was nice and the art style was original. some of the hard boiled lines were entertaining.
Personally I liked the background art, characters were so and so. Music was okay, but the lack of multiple tracks was a bit of annoying. The plot was badly handled and I hated the fact, that you could pick up some pretty random trash. The voice acting was mostly mediocre to horrible,

All in all, very disappointing game.
I'm a big fan of adventure games, and have played a lot of them. Jack Orlando, I'm sorry to say, must be among the very worst. I'll admit straight off the bat that I only played it for about 30 minutes, so it may not be entirely fair of me to comment. But I'm not particularly hard to please, and when an adventure title fails to keep me interested for more than half an hour, that says a lot more about the game than it does about me.

The art direction in the game doesn't seem professional. It just doesn't look cohesive to me, as if several artists submitted their work with noone to make sure everything sits together properly. Amateurish look.

The voice acting is laughable. Not much more to say about that.

The story, I didn't really get into, having played for so short a while.

Music. This game purports to be a "cinematic film noir adventure". So how come the music makes me feel like I'm watching softcore erotica from the 80's? It certainly doesn't belong anywhere near the 1930's.

Noir is all about atmosphere, this game doesn't have any. It's slightly comical that a game like Under a Killing Moon feels more noir than Jack Orlando.

I suspect that had the game been made in black and white, and used more suitable music, I might have stayed interested a little longer. As it is, I don't feel like wasting my time on it, and I consider myself lucky to have bought it for no more than $5,99.
i'll admit ill have to join you guys on this one, I Played for about 45 Mins and had to turn it off I couldn't stand it any more the voices, lines and very unlikable protagonist I just couldn't take any more and my standards are low (I Actually liked the latest AvP and Duke Nukem Forever)
I can't agree with you guys, it's one of the best games of my childhood. The technical side of Jack Orlando actually may have some weaknesses, but the plot, intrigue, atmosphere of Chicago, scenic backgrounds and, finally, a brilliant jazz music are outstanding!
I have to agree the voice acting is awkward, for example Jack can be talking to someone and then he sometimes talks like he is nearly crying and then the next line he is fine.

The items collections is just weird. I been playing the game for 30 mins and I already have a apple, apple core, a book, a can, newspaper, boxing gloves etc. It feels like I am cleaning up the street not collecting useful items.

I don't know if anyone had this problem but when I started the music was over powering (I can't hear the voice actors) but I think I have heard every track this game got within those 30 mins. Also have the time I don't have a clear idea on where you can go. I just found out that you can across the street.
PS I like point and click games
loon: I can't agree with you guys, it's one of the best games of my childhood. The technical side of Jack Orlando actually may have some weaknesses, but the plot, intrigue, atmosphere of Chicago, scenic backgrounds and, finally, a brilliant jazz music are outstanding!
Can't tell if sarcastic or just had a bad collection of games as a kid.
tomimt: Can't tell if sarcastic or just had a bad collection of games as a kid.
Haha, LOL! No, no, my collection was quite good ;)

Perhaps its magic has disappeared after 90's or I was just a huge enthusiast of this whole "Boardwalk Empire" climate :)
I also found Jack Orlando to be a neat game, I think it's not terrible at all (except for the voice acting).
It's actually one of the very few adventure games I bothered to play through (even if with a guide) as I don't like point-and-click adventures. I think the only other one is Telltale's Back to the Future, actually.