I think Baby It's You and Limbo are the most underrated probably because those movies don't reveal themselves until the second half. The most accessible and probably best to start with are Eight Men Out, Roan Inish, Passion Fish and then Lone Star. Lone Star is in my top ten all time and is the best original screenplay ever.
(10)-Lone Star (1996)
(09)-Eight Men Out (1988)
(08)-Matewan (1987)
(08)-The Secret of Roan Inish (1994)
(08)-Baby It's You (1983)
(08)-Limbo (1999)
(08)-City of Hope (1991)
(07)-Return of the Secaucus Seven (1980)
(07)-Men with Guns (1997)
(07)-Amigo(2010)
(06)-Passion Fish (1992)
(06)-Sunshine State (2002)
(06)-Casa de los babys (2003)
(06)-Honeydripper (2007)
(05)-Silver City (2004)
(05)-Lianna (1983)
(05)-The Brother from Another Planet (1984)

Lone Star. I also liked "Roan Inish", "Eight Men Out", "Limbo", and "Matewan".
One I have not seen but would like to is City of Hope. Where can I get it? I have it in my Netflix queue, but they have it under "Saved" because the DVD release date is unknown.
You must be the change you seek in the world. Gandhi

"Lone Star"

Matewan or City of Hope

1. City of Hope
2. Men with Guns
3. Silver City
4. Lone Star
5. Matewan

Lone Star is simply one of the best movies of all times. The American Dream, misunderstandings between fathers and sons, and mothers and daughters, race and ethnicity. What a completely wonderful film.

I love what I've seen so far, but I still haven't seen nearly enough of his work. My favourites so far then:

1. Limbo
2. Lone Star
3. Passion Fish
4. Baby It's You
5. Sunshine State

Sayles is one of my very favorite filmmakers. (Somehow that title seems more accurate for Sayles than "director.") He suggests a very strong humanity and ethical system without being preachy (or not much, anyway). He accounts for race and gender like no one else, he has a great sense of irony and humor, and he regularly gives himself juicy parts. This guy is priceless. Give him money and prizes!
Top five, off top of head:

1. Matewan (goes on fifteen minutes too long but otherwise perfect! on my short list of favorite films)
2. Men with Guns (what a compassionate, entertaining film, but a5b4lso a little nightmarish)
3. Limbo (reeks with honesty and, again, compassion; with surprises; not my favorite ending to a movie, but it does make one think)
4. Brother from Another Planet (funny, low-key, entertaining)
5. Silver City / Sunshine State (tie) (keep it up, Mr. Sayles!)

Watching right now the credits roll on Sunshine State. As usual, Sayles doesn't disappoint. But, talk about an understatement. I love this guy! And I loved this movie.
Anyway, I'm really torn between Passion Fish and Lone Star as my favorite. And I mostly choose them because I can watch them over and over again whenever either is on I always get sucked right in.

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I am actually surprised by the lack of response regarding it. My personal favorite is Sunshine State, followed closely by Passion Fish.

My favorite Sayles film by far is Men With Guns, it is just such a sweeping, epic movie.
And I agree with whoever said his most recent films have been a bit of a disappointment. There were a lot of elements I liked about Sunshine State, Casa de los Babys and Silver City, but they just weren't on the same level as his 80's and 90's movies.

Baby It's You!

Lonestar is one of the best films I have ever seen, just an amazing movie
Do not fear death only the unlived life. - Natalie Babbitt

Got to disagb68ree-just saw Matewan (finally) and was blown away.
Though Lone Star is one damn great movie

1. Lone Star (1996)
2. Limbo (1999)
3. Matewan (1987)
4. Sunshine State (2002)
5. Silver City (2004)
6. The Secret of Roan Inish (1994)
7. Return of the Seacaucus 7 (1980)
8. Casa de los Babys (2003)
   Theres still some I haven't seen, but I'm starting to think that Lone Star is the only great film he's made.

Easily Lonestar. One of the best films5b4 of the 90's. And Eight Men Out is the best baseball movie of all time.

I don't know about "best," but my favorite is definitely "Brother From Another Planet."
"Oh Benson, dear Benson, you are so mercifully free of the ravages of intelligence."

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IMO "Men with guns"
Of course, "Brother from another planet" is one of my all time favorite movies & the reason I'm a Sayles fan in the first place.

Count me on the bandwagon. LONE STAR is it. I've really liked everything else, but LONE STAR is over the top of the list. One of the very best films of 1990s.

I love Sayles' films, but for me, his best, and one of The Great American Movies, has to be "Lone Star."

I loved Limbo
But I still want to see Secret Of Roan Irish

Matewan. You know who is good, who is bad, and why. In my top 10 all time movie faves.
Secaucus Seven perfectly describes my college experience, it was like seeing the future.
Brother from Another Planet is just pure magic. It is one of those rare movies where just thinking about it can make the hairs stand up on your back.
The scene of Spano walking into the cafeteria while "Saint in the City" is playing in "Baby It's You" is one of my favorite movie scenes. Right up there with "Woke Up This Morning" as the intro song on The Sopranos as a vehicle to completely describe a character in 30 seconds or less.
I think my percentage of Chimp DNA is higher than others. Cleaver Greene