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Rupert Smith's "The Utility of Force" or Col. Hammes' "The Sling and the Stone" for a historical overview for how we got to where we are. I believe the latter is more readable.
For historical context, Mao's "On Guerrilla Warfare" (the Griffith translation is preferred) is a seminal work.
LtCol. Nagl's "Learning to eat soup with a knife" is a more academic piece comparing the successful British COIN campaign with the failed US campaign in Vietnam.
Regarding Iraq, Hashim's "Insurgency and Counter-Insurgency in Iraq" is a good, comprehensive examination of the makeup of the Iraqi insurgency.
Bard O'Neill's "Insurgency and Terrorism" is a good general dissection of insurgencies.
Gil Merom's "How Democracies lose Small Wars" is an interesting look at the difficulties democracies have in pursuing protracted, limited conflicts.
Once you get into history of specific conflicts, the possibilities are endless.
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Definitely add Galula's Counterinsurgency Warfare: Theory and Practice. I'd recommend starting with this and/or Mao. Also consider "Bing" West's The Village, as it does a great job describing the benefits/risks associated with the USMC CAP program in Vietnam and directly relates to what we're doing today. Last, maybe add Boot's Savage Wars of Peace as well. Hope this helps.
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To add a few more to the mix--look at Robert Taber's The War of the Flea, the reprint of the 1940 USMC Small Wars Manual, and its descendant, FM 3-24 (Counterinsurgency), released in December 2006 and now available commercially. You might also want to hunt down a copy of Roger Trinquier's "Modern Warfare," based on his experience in Algeria. Finally, check the October 2006 edition of Military Review, which was a special edition "Counterinsurgency Reader."
Hope this helps.
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Lawrence of Arabia
I'd definitely put T.E. Lawrence's The Seven Pillars of Wisdom on there.
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