What's sentimental lollipop?
A Google Books search finds several similes involving lollypops (or lollipops), most of them not particularly inspired. For example, from Manjusvara, Writing Your Way (2005):
- As happy as a lollipop
From Yona McDonough, Two of a Kind (2013):
It was a maple leaf—his mom was into tree identification, an interest she passed on to him—and red as a lollipop.
From Emily Bearn, Tumtum & Nutmeg: The Rose Cottage Tales (2010):
There was a fat leather steering wheel and a gearshift as big as a lollipop.
From Ava Chin, Eating Wildly: Foraging for Life, Love and the Perfect Meal (2014)
Sometimes it's nothing but a piece of paper or a candy wrapper, but this time I discovered a perfectly globe-shaped mushroom as large as a lollipop.
Really, the only remarkable lollipop simile other than Mailer's "sentimental as a lollypop" (which I must say that I don't find especially resonant, despite its skewed perspective) is the one in Irving Howe, "The New York Intellectuals: A Chronicle & a Critique," Commentary (October 1, 1968):
The new sensibility is impatient with ideas. It is impatient with literary structures of complexity and coherence, only yesterday the catchwords of our criticism. It wants instead works of literature—though literature may be the wrong word—that will be as absolute as the sun, as unarguable as an orgasm, and as delicious as a lollipop. It schemes to throw off the weight of nuance and ambiguity, legacies of high consciousness and tired blood.
What makes Howe's series of similes so brilliant isn't "as delicious as a lollipop" per se, but the juxtaposition of that sweet confection's appeal to childlike sensibilities with the powerful but almost prosaic absoluteness of the sun and the anti-intellectual quasi-adult preserve of sexual pleasure.
Mailer's "as sentimental as a lollipop" is striking, but it doesn't come from a pre-existing idiom, and it seems not to have enjoyed anything approaching widespread adoption in popular culture.
Historical footnote: Mailer on Kerouac
Norman Mailer's remarks about Jack Kerouac in Advertisements for Myself (1959) run at greater length thus:
Kerouac lacks discipline, intelligence, honesty and a sense of the novel. His rhythms are erratic, his sense of character is nil, and he is as pretentious as a rich whore, as sentimental as a lollypop. Yet I think he has a large talent.
However, Mailer subsequently became quite critical of his criticism. In Dan Wakefield, New York in the 50's (1999), Mailer seems to blame the harshness of his earlier critique on his own jealousy:
Looking back, Mailer now recalls a more personal reaction to On the Road when it came out: “I read it with a sinking heart. We were very competitive back then. I was thinking, Oh sit, this guy's done it. He was there, living it, and I was just an intellectual, writing about it.
"I enjoyed it more when I read it a few years ago, now that I was no longer competitive about it," Mailer says. "I felt I betrayed Kerouac—and so betrayed myself—when I was supposed to defend him on a TV show with Truman Capote. It was Capote's first time on TV, and he made his remark that became famous about Kerouac's work, that it isn't writing, it's typing, and that won the evening. If I was a wise then as I am now, I'd have defended Kerouac with all my ability. A half-assed defense is a form of self-treachery."
The entire episode makes being immersed in the literary life of the 1950s seem almost as appealing as living in a beach house during a massive fish kill.
Update (November 2, 2020): An early occurrence of 'sentimental lollipop'
I just came across an instance of "sentimental lollipop" as a metaphor for excessively sentimental writing. From "About Valentines," in the Springfield [Ohio] Daily Republic (January 29, 1887):
When I was fourteen years old I was wildly stuck on a little girl who lived across from where we accumulating a rent account.I dertermined to send her a valentine. I got a lovely one, with a beautiful vine clambering over it and a cluster of violets in the center. ... But the verse in it made me tired. It was something to the effect that when the starlight was kissing the moonlight and the evening zephyrs were exhaling a bouquet of of vesper odors, then I loved her—oh, I loved her. ... I knew that if I wanted to make any impression on her, I mustn't spring any Luna thou art the moon business on her, for she would simply yell across to my folks to put me on ice before I got mildewed. So I made some verses entirely of my own composure and pasted them over the sentimental lollipop.
The "sentimental lollipop" in this case was the overwrought pre-scripted poetry on the valentine, with its osculating starlight and moonlight and its odoriferous vespers. There is, however, no evidence that the author was invoking an established figure of speech with his "sentimental lollipop."