1. What are your top 3 Kubrick movies? Making this one harder with 3, not 5. Pretend that the others get burned, and you have to keep just 3 of his movies.
Clockwork Orange and 2001: A Space Odyssey top two in no particular order, can't decide between them, followed by Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb. Kubrick would have to be one of the hardest for me to pare down to just three films (similar to Kurosawa, but perhaps more impressive as he wasn't nearly as prolific). Spartacus is a good film, but I only think of it as half a Kubrick film, as it is the only one he wasn't involved with the pre-production and choice of material in the first place (a hired gun for Kirk Douglas after he fired Anthony Mann in the first week of filming over creative differences, as he admired the young director from the recently completed Paths Of Glory - maybe he also thought he could control him better due to his youth?). I found EWS to be massively anticlimactic as a final film after a 12 year interval between that and Full Metal Jacket. I wish he had been able to see AI to completion, instead (of handing off to Spielberg). Barry Lyndon was technically innovative, but imo one of his lesser works. The Killing was his first mature work, and an outstanding example of the noir genre. The non-linear, fractured chronology was one of the best attributes of the film (cited by Tarantino as a big influence on Reservoir Dogs), and actually came from the original source material novel, Clean Break. The omniscient narrator contributed to the almost clinical, documentary-like treatment of the otherwise gritty content. Paths of Glory is one of his greatest early works (prior to his trilogy of masterpieces above). Masterful camera work. The latter two are in the Criterion Collection on Blu-ray (Spartacus was on DVD, but the rights have lapsed, it did just get a recent restoration and Blu-ray release), and Killer's Kiss is included as a bonus on The Killing. Lolita not one of my favorites in his canon. The Shining was a classic in the horror genre with an iconic performance by Nicholson. Full Metal Jacket was kind of like two half movies, I thought the first half was stronger, but overall still one of his best second tier works (with The Killing, Paths Of Glory and The Shining).
2. How many movies of his have you seen?
Everything but Fear and Desire, most/all of the others multiple times.
3. What does Kubrick do well and/or what doesn't he do well?
A thousand things.
A) After he was established, he was able to secure final cut (his final home for studio distribution thought he was a genius and living treasure and were willing to work with him on terms that were acceptable to him - that was an absolute, non-negotiable), so you knew you were seeing HIS vision, pure and unadulterated. His possibly unique power in the industry extended to pulling Clockwork Orange (at least in the UK), probably an unprecedented act before or since?
B) He had great taste in material. Nabokov (Lolita) was a Nobel laureate in literature. Arthur C. Clarke was one of the towering figures in science fiction with Robert Heinlein and Isaac Asimov (also a Nobel laureate, in his case for suggesting the idea of geo-synchronous orbits so critical to modern satellite communications, Kubrick collected them like Al Davis hoarded Heisman winners and speed merchants). Burgess was one of the great British writers of the second half of the 20th century (Kubrick was born in the Bronx but became an ex-pat and settled in England), and Clockwork Orange is one of the greatest dystopian novels ever, with We, Brave New World, 1984, Darkness At Noon, etc. King is one of the greatest horror writers.
C) He was an innovator. 2001 had pioneering special effects (half decade in development) that had never been seen before. Doug Trumbull later also worked on Blade Runner, among others. It is arguably a high water mark technically and for effects in the genre to this day. Kubrick wanted to film Barry Lyndon in period correct natural light (similar to The Revenant). Sometimes he used so many candles the set caught fire! But in the excellent 2+ hour doc, A Life In Pictures , they related an anecdote about how he Frankensteined 1-2 extremely rare rear projection cameras with a Zeiss lens developed for NASA to achieve the capability of the look he was seeking. If the technology didn't exist to realize the vision in his head, he was smart enough, and resourceful enough to get the world class help he needed to create it. The Shining may not have been the FIRST, but one of the first films to employ the soon to be ubiquitous Steadicam (a specially balanced "hand held" camera that damped shaking so it looked almost like a dolly shot, but permitted more flexibility in shooting).
D) As pointed out above, he was a photographer for magazines like LIFE and TIME (not sure about LOOK?) when still a teenager, he was very precocious. Later, an enfant terrible as a young director. He was a master at composition. Like few other masters (Kurosawa, Bergman, Fellini, Tarkovsky), you could almost freeze frame ANY point of the movie, print it and hang it in your living room, it would be a work of art.
E) Camera movement (including conception and execution), one of the greatest ever. No doubt he learned well from earlier masters like Eisenstein and Welles. Max Ophuls (maybe the greatest ever virtuoso of camera movement - has at least three films in the Criterion Collection) was cited and singled out by Kubrick as an important and primary influence in this regard.
F) I liked his taste in casting, generally, and thought he made some great choices there.
G) Music. 2001 was ingenius, with the Thus Spake Zarathustra intro, Strauss waltz for the space station. The Wendy Carlos synthesizer score and theme for Clockwork Orange meshed nearly PERFECTLY with the futuristic but bleak vision of Burgess. The BIZARRE juxtaposition of classical music with the gang rumbles, and ESPECIALLY using Singing In The Rain to accompany a brutal home invasion beating and rape was one of the most subversive, provocative and disturbing choices in the history of cinema, nobody would have done that but Kubrick.
Barry Lyndon had great period classical music. When he didn't feel the Carlos score was right for The Shining (only using for the intro helicopter tracking shot driving up the Rockies), he used some cues from contemporary avant garde composers such as Ligeti, Bartok and Penderecki, and supposedly improvised sounds himself (recurring theme, see 2001 and the Frankensteined camera on Barry Lyndon in the visual domain).
H) Editing. No way he could have so many great films and overall towering stature, if he wasn't brilliant in this department.
I) Perfectionist, and it shows up on the screen. He was known to even personally visit theaters to see if the A/V equipment was working properly, a level of detail almost unheard of from major directors. He was supposedly a proponent of many takes to shape the performance he was looking for (maybe it was genuine fatigue, it sounded like he genuinely terrorized Shelley Duvall in The Shining).
4. Anything on the list underrated or overrated in your opinion?
The Killing and Paths Of Glory, they are superior to several later works, but alas, not nearly as well known. Maybe Dr. Strangelove, just in the sense I have it third, but some could make a strong case it deserves to be higher?
5. What are your favorite scenes or characters of his films?
Sterling Hayden was an iconic noir actor (Asphalt Jungle). The end of The Killing was perfect (no spoiler) and I think different from the book. 2001 had several. The obelisk on the savannah, primate learning to use a bone as a killing tool, the segue way to another, slightly more complex tool, as bone morphs to space station, HAL eavesdropping on the astronauts, becoming a murderer, the end sequence in the room. The narration of Clockwork Orange was subversive. Jack Nicholson (Here's Johnny!). Full Metal Jacket, when Pyle snaps. I have to give special props to Peter Sellers for his tour de force three character performance in Dr. Strangelove, that would have to be tops. A lot of great scenes in that, too. When Sellers realizes Sterling Hayden is insane, in talking about maintaining his essence and denying women.

No fighting in the war room.

Probably the greatest black comedy ever (though that title may belong to Kind Hearts And Coronets, about an urbane serial killer who needs to knock off more than a half dozen relatives for an inheritance he feels he was unjustly denied - all played by Alec Guiness in a Sellers-like multi-character performance, even playing a woman in one case).
6. Why did you rank him how you did?
Didn't vote in the poll. I have Kurosawa and Kubrick about tied as co-GOAT. My favorite movies are probably Blade Runner, 2001 and Clockwork Orange, as well as Seven Samurai (Rashomon up there). At his best, Ridley Scott is a master, but I find his body of work as a whole more uneven and hit and miss. I like Friedkin a lot (Sorceror one of my favorites, also did the French Connection, The Exorcist, To Live And Die In LA), but I have the same criticism of his overall body of work. Probably Hitchcock would be third for me, so many classics. The British team of Powell and Pressburger were great (Scorcese one of their greatest and most influential champions, Powell's widow was his long time editor). I'm a big fan of the work of some more contemporary directors, such as Malick and surrealists Gilliam, Cronenberg and Lynch (all well represented in the Criterion Collection).
* Good aggregate review of the nearly definitive Kubrick Masterpiece Collection
http://bluray.highdefdigest.com/13218/stanleykubrickthemasterpiececollectionamazonexclusive.html