1 down: Privates dope Florentine shrink (9)
Playful DA: dope Florentine shrink = gen Italian shrink = genitalia = privates.
25 across: Little looks at newspapers? (8)
Me and a few more liked it lots, others not so much: little looks = gazettes = newspapers.
19 down: Report wise to include dearest sort recently (9)
I loved the aural part of this clue: report wise to include dearest sort = YY to include esterda = yesterday = recently.
21 across: I’m back-to-front describing lair riders (7)
It’s DA everywhere: I’m back-to-front describing lair = AD DA describing den = addenda = riders.
These would be my top 4 as well. I love the delightful and characteristic DA mix of highbrow and lowbrow. Sometimes in the one clue! e.g. 1D the highbrow word “genitalia” and its lowbrow equivalent “privates”. And 25A I also loved. You won’t find a definition of gazette as “little gaze” in a dictionary but it’s a fun chuckle-worthy neologism. I might even start using it myself. I think if you expect DA to be absolutely pure with respect to cryptic conventions at the expense of his “playful” side, you are missing half the fun!