Being from the same studio, the same genre, the same base concept and coming out at around the same time, the comparisons to Cowboy Bebop are absolutely inevitable. Bebop, of course, went on to become an all time classic of the medium and one of the most beloved anime of all time, so it's perhaps a bit unfair to hold Outlaw Star to the same standard, and while I'm not ready to say that this is the better show- objectively, it isn't- it most certainly holds its own and is well worth a watch.
Some things this show does well include an engaging story, not taking itself too seriously, charm and humor, solid pacing and it has definitely aged well and is still super watchable two decades after the fact.
Some things this show doesn't do as well include the lack of a proper antagonist, an underwhelming ending, sometimes trying too hard/lacking subtlety/forced humor and a fairly average, forgettable soundtrack.
My overall impression and enjoyment here are far more on the positive side than the negative. Most of the things I would list as strikes against the show are nitpicks. For example in the English dub, which is what I watched, Aisha's voice really annoyed me at first. She is not human so I assume the way her voice sounds is very deliberate, but she's used as cringe-inducing comic relief initially, so I found her quite obnoxious. Over time the character grew on me and became quite useful to the crew. Another example would be stupid, non threatening names for villains such as the Macdougall brothers. Ron Macdougall at that. It instantly reminds me of Ronald Macdonald. Or maybe Mclovin' from Superbad. But either way, this man is not exactly a fear-inducing villain.
For the large majority of the show Outlaw Star does a good job of avoiding being episodic, but towards the end it starts to fall into that rabbit hole somewhat and the show starts to drag a bit. Character development leaves a lot to be desired as a whole. One could argue the reasons all members of the crew outside of the two leads choose to be there and stay there are loose at best. And, as mentioned previously, though perhaps I have a subconscious bias here because it's hard not to compare this show to Cowboy Bebop which happens to have one of the all time great anime soundtracks, but the soundtrack here isn't special or memorable- just standard anime fare.
Nitpicks and imperfections aside, Outlaw Star is an enjoyable, uptempo show with a lot of charm. I enjoyed watching it and would absolutely watch it again. If at all possible go into it NOT comparing it to Cowboy Bebop. Give it a fair chance and judge it as a standalone product. If you do, odds are you'll like what you see.
+Entertaining main story
+Charm and humor
+Doesn't take itself too seriously
+Solid pacing. Jumps right in and keeps it moving
+Strong female characters
-Drags towards the end
-Lack of proper antagonist
-Bare bones character development
-Forever in the shadow of its counterpart
OBJECTIVE RATING- 7.75-8
PERSONAL ENJOYMENT RATING- 8-8.5