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Below are all the Hellraiser movies in release order.  Next to each one I put a couple of comments and thoughts (no spoilers) as well as a ranking (1-10) on where it ranks in the franchise in my opinion.  1 being the best movie and 10 being the worst movie of the series. 
Hellraiser:  The original Hellraiser is a fairly close adaptation of the book it is based upon, The Hellbound Heart.  Most of the story remains the same.  The one noticeable difference is there are two female Cenobites in the Gash that arrives at the beginning to takeaway Frank Cotton.  Pinhead is an androgynous Cenobite that is most likely female and not the leader.  A fourth Cenobite is the leader, who is also female. The Engineer is also very different from the movie, I prefer the book variant better.

Ranking: 1. Overall, I put this as my favorite Hellraiser movie.  As the first one ever, everything is new and it is the movie that started the series.
Hellraiser II: Hellbound:  Coming in just behind Hellraiser is the sequel Hellbound.  The parts I like best about this movie is that it expanded the universe significantly.  I enjoyed continuing the story of Kirsty Cotton as well as learning more about the box and some of the back story of Pinhead.

Ranking: 2.  The expansion of the universe that surrounds Pinhead and his Gash make this secure number two spot easily.
Hellraiser III: Hell on Earth: You want more Pinhead?  This movie gives you all the Pinhead you can handle.  Although the fan favorite Cenobites are gone (Chatterer, The Female and Butterball), Pinhead does return with some new Psuedo-Cenobites.  While they are a bit of a let down, it was cool to see some new creations walking around the screen.

Ranking: 4. My least favorite of the theatrical releases, I did enjoy that it expanded on the history of Elliot Spencer and also showed some new Cenobites.
Hellraiser IV: Bloodline: While some may not like this because it hops around in time so much, I thought it was a cool concept.  Taking a wide look at LeMarchand and the history of the box added to the Hellraiser universe.  Bouncing between past, present and future gave three unique perspectives on things.  Despite bouncing around in time, this movie still fits into the continuity of the movie universe without any issues even with another six movies following it.  I know many don't like this because it is "Hellraiser in Space" but I actually think they pull it off pretty well...although not sure why they had to be in space for the ending, it did seem a little unnecessary.

Ranking: 3.  I love when story lines come to a conclusion so I put this one high up on the list.  It was the only Hellraiser I saw in theaters so maybe I have overly fond memories of the experience.  I honestly thought about ranking it higher but the first two started everything so I dropped this one to number 3 spot.
Hellraiser V: Inferno: The first time I saw this my roommate in college was watching it without me.  I walked through the room and asked what was going on.  He gave me a 30 second synopsis of the movie so far and explained that mysterious things were happening.  Without seeing any of the movie I told him what was going on. 

Ranking: 10.  The whole movie felt like it was trying to give you this big twist ending but if you are even remotely familiar with the Hellraiser franchise, the ending seemed pretty obvious.  This was the first straight to video Hellraiser movie.  Going from the budgets of 2-4 to this one is a rough step and if it wasn't a Hellraiser movie I would have turned it off.
Hellraiser VI: Hellseeker: This felt like I was just watching Hellraiser V again.  The only saving grace in this movie is Kirsty Cotton has a role in it (same actress too).  The only part I enjoyed was the last 10 minutes of the movie, where the back story of Hellraiser and Kirsty Cotton's future actually advanced a little.

Ranking: 8.  Without Kirsty, I would have dropped this one lower, but I like seeing what happens in the future of one of the beloved characters from the franchise.
Hellraiser VII: Deader:Another straight to video movie that was trying to set up a big twist. 

Ranking 9:  I didn't enjoy this.  Hellraiser V through VII all felt rough.  This one was at least a little more complicated than V and VI.  However, without Kirsty or someone to advance the overall story of the Hellraiser franchise it dropped to seven in my ranking.

Hellraiser VIII: Hellworld: Looking at the cover, I was looking forward to this one the least. Plus, add in extreme lowered expectations after watching V through VII and I was expecting a disaster.  It actually was pretty interesting.  Not your typical Hellraiser movie and a unique take on the franchise.  I can see some people hating it but honestly it kept me engaged and I thought the ending was interesting at least.  Having Hellraiser as a pop culture icon via video game was cool because we didnt have to go through the process of movie charecters being confused about the box, Pinhead and more.  It sped up the timeline of events in the movie allowing the movie to jump into action faster.  While it felt like they just slapped the Hellraiser brand on a movie that was already written, V through VII all felt like that, so I actually didn't mind it that much.

Ranking 7:  Below all the theatrical releases but definitely above V through VII.  It was a good movie and the only one of the straight to video Hellraisers that I have actually watched more than once.

Hellraiser IX: Revelations: I was a little worried I was about to watch an all "found footage" movie when it started off, which always gets ridiculous as they try to explain why someone is video taping large portions of their day.  However, the movie did a good job of cutting between found footage and normal film.  This was the first movie since the theatrical releases that felt like a Hellraiser film to me and not just a script that they slapped the Hellraiser brand onto. 

The plot had plenty of small twists and I enjoyed how it showed a darker side of characters who all seem innocent at first glance.  There are several callbacks to the original movies and the movie kept my interest without dragging on too long.  Overall, I enjoyed it. 

Ranking 6.  I could see some people putting this one higher on the list.  The practical effects were great to see in a movie industry now dominated by CGI.  I wasn't crazy about the new Pinhead but it's hard to replace someone I've grown accustomed to through eight other movies. 
Hellraiser X: Judgement: The first big thing to note about Judgement is that this is the 2nd Hellraiser movie without Doug Bradley and a different pinhead that was in Revelations.  That being said, I think the new actor did a good job of filling Doug's shoes although it still felt wrong watching a Hellraiser without Doug Bradley.  

Overall, Judgement was interesting and engaging for the entire length of the movie.  My favorite aspect of it was it was the first movie to make overt Christian references in it and even introduce the audience to one of the archangels.  On the 10th movie they finally acknowledged God and Hell's subordinate role to Heaven.  The movie isn't 100% theologically correct (nor is anything else in the Hellraiser universe), however I enjoyed a movie that finally expanded the overall universe of Hellraiser, which was really the first one to do so since Bloodline (IV).  

Ranking 5.  This is the best straight to video Hellraiser movie in my opinion.  I think 8, 9, and 10 are all close in quality and are all a big step above 5, 6 and 7.  However, they all rank below the theatrical releases in my opinion.

Forces of Hell:

This is a Hellraiser and associated properties fan site.  Videos and pictures are property of the original content producer. When possible, it is also meant to educate followers about the Orthodox Church by mixing in fiction (the world of Hellraiser) with fact (Orthodox Christianity).