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I watched this entire series over the past summer, mainly because I'm such a big fan of Lionel Barrymore, but as I watched the series I came to like Lew Ayers as well. I just decided to compile this list for fun, to see if I could fairly rank the films from best to worst. I'll make a second list later on, ranking the Gillespie films, made after Lew Ayres left the series.

A list by barrymost
9
Items on this list61%
Average Rating12h 16m
Total Runtime$0
Total Revenue1
Dr. Kildare's Wedding Day
My favorite of the series. But not only because of the story (which was very sad), but mostly due to the musical theme in the plot, and the fact that Lionel Barrymore composed the music for the film.
Movie
August 22, 1941
1h 23m
$0
2
Young Dr. Kildare
The original. A very entertaining film in itself, the fun was just beginning, and this series had great continuity for its time.
Movie
October 14, 1938
1h 22m
$0
3
Dr. Kildare Goes Home
Good story and writing, not as outlandish as some of the other installments. Except for the crazy ending which makes absolutely no sense, but it's still a hoot!
Movie
September 6, 1940
1h 19m
$0
4
The Secret of Dr. Kildare
Probably the most unashamedly comedic film of the lot. Gillespie's over the top (as usual), and it's just a lot of fun.
Movie
November 24, 1939
1h 24m
$0
5
Calling Dr. Kildare
Where Dr. Kildare first meets his true love...and Lana Turner, too!
Movie
April 28, 1939
1h 26m
$0
6
The People Vs. Dr. Kildare
A semi-serious, entertaining courtroom drama/comedy. Will they really call Dr. Gillespie to the witness stand?
Movie
May 2, 1941
1h 18m
$0
7
Dr. Kildare's Victory
The entry right after "Dr. Kildare's Wedding Day" this is another example of the good continuity, as the good doctor is still very much affected by the events from the last film. However, it does end up being much more lighthearted that I expected. Some corny, ridiculous moments, of course, but also some good wisecracks from Gillespie.
Movie
February 4, 1942
1h 32m
$0
8
Dr. Kildare's Crisis
Okay entry in the series, the title crisis was a tad far-fetched, with the medical angle and some of the emotional motivations being clumsily handled. But, we do get to hear a little bit more of Dr. Gillespie's background, and his scenes are always the best.
Movie
November 29, 1940
1h 15m
$0
9
Dr. Kildare's Strange Case
One of my least favorites out of the nine films with Lew Ayres. Just didn't really resonate with me, especially since the preceding three were very good. Though Gillespie, of course, still gets all the great laugh lines, and delivers them perfectly.
Movie
April 12, 1940
1h 17m
$0