Below are the books I've read thus far, and of which I recommend. All of these I've read at least once. I will update this list from time to time as I read more…

Plain Secrets: An Outsider Among the Amish
Mackall, Joe

The Riddle of Amish Culture (Center Books in Anabaptist Studies)
Kraybill, Donald

Growing Up Amish: A Memoir
Wagler, Ira

My Amish Childhood: A True Story of Faith, Family, and the Simple Life
Eicher, Jerry S.

Called to Be Amish: My Journey from Head Majorette to the Old Order
Miller, Marlene C.

Plain Faith: A True Story of Tragedy, Loss and Leaving the Amish
Eash, Ora Jay and Irene, with Goyer, Tricia

Becoming Amish: A Family's Search for Faith, Community and Purpose
Smith, Jeff

My People, the Amish: The True Story of an Amish Father and Son
Keim, Joe

Our Amish Neighbors
Schreiber, William I.

A History of The Amish
Nolt, Steven

Success Made Simple: An Inside Look at Why Amish Businesses Thrive
Wesner, Erik

Broken Roads: Returning to My Amish Father
Wagler, Ira

The Odyssey of a Heart: Innocence, Drugs, and the Pursuit of Freedom
Wagler, Mervin

Money Secrets of The Amish: Finding True Abundance in Simplicity, Sharing, and Saving
Craker, Lorilee

Amish Peace
Fisher, Suzanne Woods

The Amish Struggle with Modernity
Kraybill, Donald B. & Olshan, Marc A.

Amish Society (Fourth Edition)
Hostetler, John A.

The Amish In their Own Words: Amish writings from 25 years of Family Life magazine
Igou, Brad (Compiled by)

The Amish Way: Patient Faith in a Perilous World
Kraybill, Donald; Nolt, Steven M.; & Weaver-Zercher, David L.

Living without Electricity: Lessons from the Amish
Scott, Stephen & Pellman, Kenneth

Motion pictures:

The Amish: Shunned (Digital) PBS
Callie T. Wiser (Writer, Producer, & Director)

The Amish: The Truth Isn't Plain or Simple (Digital) PBS
David Belton (Writer, Producer, & Director)

Amish: How They Survive (DVD)
Burton Buller

The Amish: Back Roads to Heaven (DVD)
Burton Buller

Not necessarily Amish themed, but related…

Transforming the Believer (book)
Eicher, Jerry S.

The Naked Anabaptist: The Bare Essentials of a Radical Faith (book)
Murray, Stuart