"Wanna Take You Higher..." 
Giant legend OTT
Flop with fins EDSEL
Ink spots, briefly? TATS [hip for tattoos]
Theme: words that rhyme with “higher” used in familiar phrases now changing meaning
Sign some new sluggers? HIREPOWER
Stand-up gig for Richard? PRYORENGAGEMENT
Instrument in need of cleaning? DIRTYLYRE
Augustine for one? DEEPFRIAR
This puzzle stretches one’s knowledge of widely divergent fields: from EROICA’s birthday to DANNO and Chin Ho; from AGNI to MOORE; from ROS to Nagpur; from TATS to “The Lonely Goatherd”; etc.
Word with time and space WASTE [“waste of time” is common but not “waste of space,” so I feel the clue is a bit too broad]
RATING:
Three grins = Excellent: Loved it; Two grins = Good: Enjoyed it; One grin = Satisfactory: A bit bland for my taste; One teardrop = Unsatisfying: No fun
