Sorry, I am late to the party as always, but anyways.. I have to say, I enjoyed both films, but I think Confessions is the better of the two. Both movies had their strengths and weakness, but i think Confessions had the more dirty and dark atmosphere, very gritty, good music score and more true to the real life Henry, even look wise. Yeah, both were good flicks, but this one is more nightmarish in my opinion.

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Henry is the superior, more powerful movie; however this film is highly underrated and stays with you too.

It's unfair to compare the two. CONFESSIONS OF A SERIAL KILLER and HENRY - PORTRAIT OF A SERIAL KILLER are two entirely different movies. John McNaughton created his own story with HENRY by taking a simple plot and blending it with elements of the original story. Henry and Otis in HENRY are different characters altogether. Just because they share the same names doesn't mean they're supposed to be Henry Lee Lucas and Ottis Toole. HENRY takes place in Chicago while Henry and Ottis committed their murders in Texas and Florida. CONFESSIONS OF A SERIAL KILLER is directly inspired by the murders.
To the world you may just be somebody, but to somebody you may just be the world.

This film more close to Henry Lee Lucas than Henry portrait of a serial killer.

Henry: Portrait of a Serial Killer is much better but that's not to say Confessions is a bad movie, its a good one actually 6/10
When there's no more room in hell, The dead will walk the earth

Yes. This is why I like confessions better because it is more true. Hell both the killers look just like the real killers and the murders were close to the original ones.

I like Confessions better. It was definitely creepier, and seemed like it would be more true to life. It makes you think about mans inhumanity and what
causes it. The Heny:Protrait movie is unrealistic because you cannot
image Henry looking like a Hollywood actor. Also, the Henry:Portrait
movie threw in this bogus scene of Henry killing Otis which never
happened. Henry had no such redeeming actions. This movie had the most
disturbing rape/murder scene ever filmed. I don't know if that makes it
a good movie or a bad movie, but you cannot forget it.

Henry usually will be called better, because it was the film that was critically recognized and Michael Rooker is a recognizable face. It seems that the critics were sleeping the year before when Confessions came out.

That's because "based on" does not mean irrefutable biographical account.

It is amusing for fiction but there are tons of inaccuracies concerning Henry and its sequel.

Nine out of ten people on the Henry message board will tell you 'Henry' is better. That's a load of crap though. Henry: Portrait is boring, slow-paced, and not really interesting. I honestly yawned my way through it.
Confessions, on the other hand, is a pretty good low budget movie. I've watched it and rewatched it a few times. I'll stick with this one over Henry any day.