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Intellectual Dissident 101:

Preamble:
--I first heard of Chomsky from an interview by Rage Against the Machine's vocalist which was bonus material in one of their live concert DVDs. Back then I was an apolitical teenager in Canada (thus, a default liberal, i.e. cosmopolitan capitalism) and had no idea about the interview topics (other than a feeling that they were “c�DzԳٰ��DZ��������������).
--Despite some false starts, Chomsky's Hegemony or Survival: America's Quest for Global Dominance flipped my liberal geopolitics back to reality, as Chomsky became my introduction to critical thinking on politics, synonymous with "intellectual" and "dissident".

The Good:
--Some critique Chomsky's presentation style, from his dry writing style to his chalkboard eraser speech. If I could guide my apolitical past-self, this book would be the first work by Chomsky to start with. It's a superbly edited volume of his most concise lectures (including Questions/Answers with audiences, always useful).
--The essential Chomsky:

1) Media literacy:
--This is the first tool for beginners trying to learn how the world works.
--Crucially, it's not as simple as saying all of "mainstream media" is "fake news", like how Trump reactionaries cherry-pick what they want to hear and conjure up fantasies for everything else!
--Propaganda is usually more nuanced, and so is fact-finding. Capitalists need certain facts to run their businesses, so business news targeting them are often filled with useful information. The manipulations come with how things are framed, so op-ed opinion pieces are often more unhinged. So, it's important to consider the target audience and various biases.
--Chomsky has a useful set of lectures on this, including the role of the intelligentsia, how our assumption of public opinion is mis-framed, etc., in: Necessary Illusions: Thought Control in Democratic Societies
--Similar principles should be applied to international news, where foreign outlets offer certain insights. For case studies in US media coverage of foreign policy, see Herman/Chomksy's famous Manufacturing Consent: The Political Economy of the Mass Media

2) Power: Private vs. Public:
--Power must prove its legitimate uses: Chomsky's political roots are in anarchism/libertarian socialism (see later for other perspectives to consider).
--Democracy under capitalism is restricted and contained in the political theatre, where the public are mere spectators. This is why the public need to build social movements to pressure the political theatre. Meanwhile, capitalist power is in the private sphere where finance and industries rule the economy.
-The Corporation: The Pathological Pursuit of Profit and Power)
-The Democracy Project: A History, a Crisis, a Movement
--Of particular interest is the changes in activism: how mild the anti-war movement was during the war on Vietnam (i.e. "we should stop because we are losing") and how it progressed and forced the US elite (i.e. "Vietnam Syndrome") to rely on its own clandestine terror agencies, funding other mercenary states/groups, and replacing the draft with a mercenary army:
-Washington Bullets: A History of the CIA, Coups, and Assassinations
-The Jakarta Method: Washington's Anticommunist Crusade and the Mass Murder Program that Shaped Our World
-A People's History of the United States
--Since this is a collection from 1989 to 1999, it misses the War On Terror and beyond. However, the foresight demonstrated throughout the topics further cements the methodology/conclusions (including a good bit setting up the election of Trump!).
-The Management of Savagery: How America's National Security State Fueled the Rise of Al Qaeda, ISIS, and Donald Trump
--Despite complaints of government overreach, this complain is only when the public pressures for crumbs of redistribution. There is no complaint for all the essential services the government provides to make capitalism operational:
i) violent enforcement of capitalist property rights, including the global division of labour (military) and domestic (courts/prisons).
ii) long-term research and development
iii) physical infrastructure
iv) social infrastructure: education
v) reproduction of system (including social consent), demand management, clean up after crises
...see


The Missing:
1) Historical Materialism:
--While Chomsky does sometimes reference Marx/Marxist historical materialism, his anarchist leanings seems to bias him to leave this for Marxists (similar with Graeber, ex. The Dawn of Everything: A New History of Humanity). Indeed, Chomsky seems to cite Classical Liberals (ex. Adam Smith) more than Marx; while I enjoy Chomsky flipping Smith around vs. today's vulgar economists, this does contribute to Marxists calling Chomsky a "liberal".
...So, as an introduction, there's a huge gap that needs to be filled. I.e. the changing material conditions and how this affects political bargaining power, ex. the World Wars forcing women and racial minorities (esp. black, given US history) into the professional workplace, inadvertently facilitating mass social mobilization for feminism and Civil Rights.
...Luckily, there's just for this, especially episodes:
-"6. Political Anthropology: When Communism Works and Why | What is Politics?"
-"7. The Origins of Male Dominance and Hierarchy; what David Graeber and Jordan Peterson get wrong"
-"7.1 Material Conditions: Why You Can't Eliminate Sexism or Patriarchy by Changing Culture"
-"8. Materialism vs. Idealism: How Social Change Happens | What is Politics?"

2) (Geo)political Economy:
--With Chomsky's (geo)political framework, I would then recommend the following for "the Economy" (which my past self was even more lost in with its abstractions and misdirections):
i) Ties history with economic conditions: The Divide: A Brief Guide to Global Inequality and its Solutions
ii) Lifts the veil of "economics" to consider its fascinating paradoxes: Talking to My Daughter About the Economy: or, How Capitalism Works—and How It Fails

The Questionable:
1) On Marxism/Leninism/real-world socialism:
--While I still find light-hearted humor with Chomsky's quips about not knowing what “dialectics�� and “praxis�� are, his one-liners like "the USSR was a dungeon" (maybe not from this volume but you'll hear it if you follow his lectures) seem counter-productive for an US audience so paranoid with Red Scare perversions of historical context.
...US audiences need a hearty dose of the following:
i) Vijay Prashad (Struggle Makes Us Human: Learning from Movements for Socialism):
ii) Michael Parenti (Blackshirts and Reds: Rational Fascism and the Overthrow of Communism):
iii) Utsa Patnaik (Capital and Imperialism: Theory, History, and the Present):
iv) Radhika Desai:

2) There was a strange bit about capitalism being against racism:
--Here is how it went:
i) Race is a human construction.
ii) Capitalism is anti-human, in that it wants humans to be reduced to interchangeable cogs.
iii) Now, in the short-term, racism may be advantageous, but in the long-term capitalism will work against racism.
...Now, this may be just a small rhetorical remark and I do get Chomsky's surface logic, but I find such grand philosophical musings to be vague and distracting. I would say there are strong examples throughout history to today where various forms of racism are directly exploited and magnified by capitalism for divide-and-rule (which fits with capitalism's abstraction of social relations, ex. global division of labour).
...And I do not see how one can classify short-term vs. long-term implications here, when it is foundational to your argument. For more on time as a unit of analysis, see: World-Systems Analysis: An Introduction.
...Could Chomsky's interpretation be too focused on idealism (race = human construction) and lacking analysis of materialism? See the "What is Politics?" episodes I listed above, especially the last 2.
...There are plenty of theories on capitalism and racism that I find more useful, from classics like Eric Williams' (later the first prime minister Trinidad and Tobago) Capitalism & Slavery to Gerald Horne's modern interpretations.
...Same can be said for capitalism and patriarchy, esp. care-work/"social reproduction":
-The Invisible Heart: Economics and Family Values
-Feminism for the 99%: A Manifesto
-Caliban and the Witch: Women, the Body and Primitive Accumulation