One needs to distinguish between popular philosophy and philosophy proper which serves different needs. This division I think is evident in almost, if not all the arts & sciences.
But one must also distinguish between popularising, which is making a complex topic intelligible to the people, and an art in itself, from banalisation, which loses the essential thought or impetus. In its most slimmed down form one thinks of here the proverb & the aphorism, the latter being a respectable literary form - Rouchefaucauld & Nietszche used the form, for example.
Popularisation, to paraphrase Einsteins aphorism on Occams Razor, is to make everything simple but not simpler. And noticing the form of the aphorism, to make things art-full and not art-less. (Physics is full of art & aphorisms, though this point is missed by many, there, they're thought of a kind of folk-lore rule-of-thumb).
Alice in Wonderland plays tricks with logic, language and reality, but with such disarming simplicity that it has become a childrens classic. One could argue that myths & fairytales encode such thoughts too. Prometheus and the fire encoding the drama of self-consciousness, Saturn devouring his children - generational conflict, and inverted in Kings Lear, where the children devour Saturn, and sleeping beauty - does one need Freud to decode its meaning, or was its meaning there already all along?
A thought then presents itself: what distinguishes between the sound-bite, the jingle & the aphorism? One might suppose the sound-bite sells an obviously local phenomena, a party political message or a new brand of saucepan. Whereas the the aphorism is thought-provoking on issues of wider import. Wildes apohrism on 'knowing the price of everything and the value of nothing', can be usefully interpreted for example, as an attack on utilitarianism, or mercantilism. They encode, despite appearances, profound thought. Nagarjunas, Verses from the Centre, are essentially aphorisms strung together, and take an entire secondary literature to decode.
Pop Art as High Art was done by Andy Warhol. His art was perverse in that it seemingly celebrated the banalisation of art. Its mechanisation. Its automation and flat & high affect. These attack the primary attibutes of art as written and described in Benjamins The Work of Art in the Age of Mechanical Reproduction.
Warhol used Primary colours. Bold outlines and bold themes. By decontextualisating Marilyn Munroe & Chairman Mao one could say he was commenting on the Commodification of Spectacle - by the cinema and the news broadcast - moving on from Debords Society of the Spectacle. His prophetic fifteen minutes of fame has found its fulfillment in the age of facebook, youtube & celebrity. His silent film Blowjob, reflects on the banalisation and repetition of a sex-act, which looks ever-more prophetic in modern western cultures fetishisation of the body to the purely physical locus of the performed sex-act.
Romanos rationale for America as a Philosophical People is very reminescent of enlightment values, and possibly only those dressed up in fashionably modern garb. In which case one should ask, taking the French Revolution as a nominal index for that point of departure in thought, one should ask has the Western World become a more Philosophical World since 1789? By what means and measure can one begin to answer this question? Has the new philosophy of the few only become the new dogma of the many? One rather has the impression rather that the philosophy as an end-in-itself is looked on as an eccentric habit, cultivated by a few, and whilst respectable, of no serious import.
An answer to Romano, might be with Toquevilles Democracy in America
Tocqueville warned that modern democracy may be adept at inventing new forms of tyranny, because radical equality could lead to the materialism of an expanding bourgeoisie and to the selfishness of individualism. In such conditions we lose interest in the future of our descendents...and meekly allow ourselves to be led in ignorance by a despotic force all the more powerful because it does not resemble one.
One thinks here in America, also of Chomskys Manufacture of Consent, Edwards Bernays spinning of Propaganda into Public Relations and Ayn Rands appropriation of Aristotelian virtue ethics into a heady mix of individualism & homo economicus. The predominance of American think-tanks in Climate Change Denial, and the current revelations of mass-surveillance.
Interestingly, one might suppose, that cultural products like the X-files are popular expressions of being led 'in ignorance' by inscrutable forces.
Tocqueville worried that if despotism were to take root in a modern democracy, it would be a much more dangerous version than the oppression under the Roman emperors or tyrants of the past who could only exert a pernicious influence on a small group of people at a time
Of course history has borne out Toquevilles worry, as Germanys nascent Democratic traditions were subverted by Nazism, in Italys by Facism and in Russia and China by State Communism.
But to come back to your headline question, popularising philosophy isn't philosophy proper but is in itself an art-form; its degenerate & decadent forms are generally pop-cultural fodder or kitsch philosophy - on the level of Yoda in Star Wars.