Relative difficulty: Medium-Challenging
THEME: ... with "The" — Theme clues all end with the phrase "with 'The'" (a common crossword direction), but in this case, the direction is literal, i.e. you have to supply the letters "THE" at the beginning of the answer to make any sense of it

Word of the Day: ANTONIO Prohias (14A: Original "Spy vs. Spy" cartoonist Prohias) —
Antonio Prohías (January 17, 1921 – February 24, 1998), born in Cienfuegos, Cuba, was a cartoonist most famous for creating the comic strip Spy vs. Spy for MAD Magazine. [...] Although he is most famous for Spy vs. Spy, the majority of his comic strips, such as El Hombre Siniestro, La Mujer Siniestra, and Tovarich, were published mostly or only in Cuba. Altogether, only about 20 of his roughly 270 contributions to Mad were of anything other than the spy series. As a result, most of the available information on this other work comes from the Spy Vs Spy Complete Casebook (Watson-Guptill, 2001). (wikipedia)
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I can see how someone might have found this enjoyable and clever. I'll give you 'clever,' esp. for the initial gimmick idea. But the execution of that gimmick just rubbed me the wrong way.
Theme answers:
- 19A: Churchill subject, with "The" (IR FINEST HOUR)
- 30A: Rodgers and Hart song, with "The" ("RE'S A SMALL HOTEL")
- 36A: George C. Scott movie with a rock band namesake, with "The" ("EY MIGHT BE GIANTS") — this is where I picked up the theme, because it's the first theme answer I knew. Before that, I assumed there was some kind of IOU theme ... because the "I" from BASIC (1D: Computer language from 1964) appeared to be where an "OU" should be in the Across answer: [OU]R FINEST HOUR. But no...
- 48A: Hit movie of 1991, with "The" ("LMA AND LOUISE") — so, two movies and a song and a ... subject. Nice tight grouping [/sarcasm]
Bullets:
- 7A: Rum-enhanced dessert (TORTONI) — not familiar. Sounds like pasta. Easy enough to piece together from crosses.
- 58A: Big band brothers (DORSEYS) — adding to the decidedly olde thymey flavor of this thing. Had trouble here primarily because I had BAHRAIN as the answer to 37D: Its coat-of-arms includes a marlin and a flamingo
- 8D: Topic of Weird Al Yankovic's "The White Stuff" (OREOS) — never heard of it. Have heard of Weird Al's other White song: "White and Nerdy"...
- 13D: Lemieux milieu (ICE) — Mario Lemieux. Former hockey great and current owner of the Pittsburgh Penguins.
- 26D: Utterance from Reagan mimics ("WELL...") — this made me laugh, though ... for anyone not at least a teen in the 80s, good luck.
- 44D: Clothing company since 1992 (FUBU) — haven't seen, thought about, or heard of FUBU in what seems like at least a decade. Forgot it existed. I associate the brand with mid-late-90s hip hop.
- 46D: Actor who played himself in 1988's "Moon Over Parador" (ASNER) — no idea, but ... when in doubt, guess ASNER.
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