The best places to start are a 2009 BBC documentary series entitled "Iran and the West" (parts 1, 2, and 3), and a 2013 New Yorker article entitled The Shadow Commander. In the latter article, author Dexter Filkins focuses his narrative on Major General Qassem Suleimani, commander of the Iranian Revolutionary Guards Corps' Quds Force - the Iranian corollary to the CIA's Special Activities Division. If you ignore everything else, you ought to invest some time in those four items. Beyond these resources, what follows are some topical sections on various aspects of Western-Iranian relations since 1979.
The Iran-Iraq War
Mark Bowden's Guests of the Ayatollah provides some of the best discussion of the Iran Hostage Crisis and the early stages of the Iran-Iraq War that I've ever read. Before I go into detail, here's a brief, oversimplified synopsis of the Iran-Iraq War and its aftermath.
Though little-known to Americans, post-Revolution American-Iranian relations deteriorated further as a result of the The Tanker War, notable elements of which were Operation Earnest Will, Operation Prime Chance, Operation Eager Glacier, Operation Nimble Archer, and Operation Praying Mantis. The last of these was a direct response to the Iranian mine strike on USS Samuel B. Roberts. Relations were further complicated by the accidental American shootdown of Iran Air Flight 655 by USS Vincennes.
Support to Insurgent and Terrorist Groups
Beyond its prominent role operating Hezbollah in Lebanon and elsewhere, and supporting other groups such as Hamas, Iran's role in and relating to Afghanistan and Iraq have been complex. As noted by Dexter Filkins in the article linked above, Iran nearly went to war with Afghanistan prior to 9/11, and Iranian and Western forces cooperated in Afghanistan against the Taliban in 2001 and early 2002.
However, after relations deteriorated once more, the Iranians subsequently appear to have provided some support to both the Taliban and al Qaeda. This has apparently involved providing al Qaeda with logistical assistance and safe havens, and possibly supplying weapons to the Taliban.
The Iran/al Qaeda relationship has been tenuous, and has backfired upon both Iran and al Qaeda at times. The article about Qassem Suleimani notes that initial cooperation with al Qaeda in Iraq eventually collapsed, fueling the Sunni/Shiite sectarian war that took place over the course of several years. Iran supplied specialized weapons to Shiite insurgents...
... and simultaneously kept several members of Osama bin laden's family in Iran.
There are a couple of other articles about Iran and afghanistan that are worth reading:
Iran and the Gulf
I could probably write a book on recent relations between Iran and its relations with the various neighbors. Having already skirted around the situation vis a vis Iraq, here are a few articles discussing recent interaction, mostly adversarial, between Iran and Bahrain, the only Shiite-majority GCC member...
... Qatar and the United Arab Emirates...
... Kuwait...
... Oman (whose relations with Iran remain the closest of the Gulf nations due to a variety of factors specific to Oman)...
... and Saudi Arabia.
The West is frequently criticized for its close relations with the GCC's authoritarian regimes. After the 1979 Islamic Revolution, relations between the West and the GCC states solidified due to the mutually adversarial relationships between Iran and both parties. (This was later strengthened by distrust of Iraq, but that's another topic for another day.) People tend to focus on Iran's nuclear program with respect to its actual potential destructive capacity and range. While these concerns are legitimate, Iran's tendency to eschew direct confrontation in favor of more covert, irregular methods demonstrates that the underlying concern should be how a potential Iranian nuclear capability might be used to advance Iranian political objectives in the region. One major concern is that an Iranian nuclear capability would compel the Saudis, and potentially the Egyptians and the Turks, to pursue their own nuclear programs in order to deter Iran's influence. (I'm working on an upcoming post that will focus specifically on this issue.)
American Relationships with Dissident Groups
While in no way claiming any moral equivalence between Iranian support for terrorist groups, and American support for the following groups, it's worth noting that Iranian distrust of the West typically takes Western support for such dissident groups into account. (There's a sort of chicken/egg dichotomy that's worth noting on that one.) There have been suggestions of covert Western support to the Balochi insurgent group known as Jundallah, formerly led by the late Abdolmalek Rigi...
... and Western states have openly worked with the Mojehedin e Khalq (People's Mujahideen of Iran), a leftist group that worked with Iraq during the Iran-Iraq War and subsequently took asylum in Iraq at Camp Ashraf until relatively recently.
There's obviously a lot of information to go through, and it could easily take a person days or even weeks to try and read or process it all. These items are barely scratching the surface of these issues. The relationship is complicated, it's always been complicated, and it will remain complicated. People like things to be wrapped up neatly and tidily - we're conditioned by books, movies, and television to expect that. In truth, Western States have strategic goals that compete directly with those of post-Revolutionary Iran. It's difficult for any expert to identify significant opportunities for compromise and cooperation, or to foresee a future in which those strategic goals will overlap. As such, and despite pronouncements and celebration of deals over Iran's nuclear program - and judging from the nightly rhetoric on Iran's Voice of Justice broadcasts - the underlying conflict between Iran and the West will continue into the foreseeable future.
