Each of the clues must be interpreted phonetically, "Anguished English" style to be understood. Each clue clues an answer which can be phonetically represented by two letters. The complete list of clues and answers is below.
PRETEND SHUSH ARTY RT (Pretentious)
TILL TED TUDOR SIGHED ASKEW SQ (Tilted to the side)
WRY DUH WAKE APT INN AYE-AYE II ("Right away, Captain")
PAPER RED ASSESSOR AYIN IN (Pei predecessor)
SHY NEONS MAUL ASSIZE BEADY BD (Shint and small, as eyes)
ASH AFT TOUGH FLIGHT BEAM BM (A shaft of light)
DISK OWES RAW BIN BARRIER MOW REESE BEEGEE BG (Disco's Robin, Barry, or Maurice)
KEY PINGS EGRET STEW ONCE ELF CAGEY KG (Keeping secrets to oneself)
FAY MUST RYE COW VICK TIM CASEY KC (Famous strikeout victim)
UH NET RACK TIFF PURSE IN CUTIE QT (An attractive person)
ARE TIN THAI TILL BIDE ANNULLED RUMP DEAL DL (Art in title by Donald Trump)
YANK EASE TART ENSURE STOP DIDI DD (Yankees' starting shortstop)
ATE TIVO LOU SHUN POE CHEM ON EEVEE EV (Eight-evolution Pokemon)
FOR TEA THYME STEW EIGHTY AT (Forty times two)
TOCKS YOHOS TESTY JEN HEIRESS ELLEN LN (Talk show host DeGeneres)
KOCH NIECE SCREE TING 'ELLO LO (Cockney's greeting)
UH PENNED TOOTH HUB OFFER ENQUEUE NQ (Append to the buffer)
ADE ED LEASE INN ENVY NV (A deadly sin)
GERM MENS IT TEEN AYN THIN SIGHS ESSEN SN (German city, ninth in size)
MY CROWS OFF TOFFEE SCUM PWN INT EXCEL XL (Microsoft Office Component)
ONCE HOOD ENT RINKED TOOTH HISS EXCESS XS (One shouldn't drink to this)
FRA STINK RUSTED ICY IC (Frost-encrusted)
YEA LORD ART MUFF IVY IV (Yale or Dartmouth)
KERR LEAVE EDGE TAB ALIKE AB ITCH KALE KL (Curly vegetable like cabbage)
THAI PUFFED AWL WHIFF IN ORE MUSS SAID KEWPIE QP (Type of doll with an enourmous head)
GRAN KNOW LULL IKE OATY OT (Granola-like)
LIEU QUILL SUNS BROTH HER OWEN ON (Luke Wilson's brother)
FOUR MERP ITCH URGE ACHE PEAVY PV (Former pitcher Jake)
BAR SELL OWNERS CENT HERB ACK PIQUE PK (Barcelona center back)
SQUAW LITTER MORE LEAD EAGER RAIDED SEEDY CD (Squalid or morally degraded)
AURA COLOR SIGH KICK SEER CR (Oracle or psychic)
FORTH GULL DENT TICKER TWIN ER TEAVEE TV (Fourth golden ticket winner)
DE WRING THUS AIM PEER YOD WHILE YL (During the same period)
BOWL JUROR HERS ARGH WHITEY YT (Bulger or Herzog)
INN TENTS REEL LEDGE US DEVO SHIN ZEAL ZL (Intense religious devotion)
There is exactly one way to fit these answers into the provided grid such that any two adjacent words share a letter across their adjacent edge, and that it is as follows:
The answer is GLADDEST.