I hope that you enjoyed Saturday's Mac Riddles, episode 261. Here are my solutions to them.
1: From the Golden Gate it first appeared in El Capitan and now rules them all as SF.
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San Francisco
From the Golden Gate (in San Francisco) it first appeared in El Capitan (the font was released in 2014 and became the UI font in El Capitan) and now rules them all as SF (known now as SF or SF Pro, it's standard across all Macs and devices). See Wikipedia.
2: For 15 years, Bigelow and Holmes' great clarity coped well with bitmaps.
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Lucida Grande
For 15 years (1999-2014), Bigelow and Holmes' (it was designed by Charles Bigelow and Kris Holmes) great clarity (its name is derived from 'lucid') coped well with bitmaps (it did). See Wikipedia.
3: Swiss novel that only starred for one year in Yosemite.
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Helvetica Neue
Swiss (hence 'helvetica', by the Swiss type designer Max Miedinger) novel (new = neue) that only starred for one year in Yosemite (it was the UI and system font for just Yosemite, before SF was released). See Wikipedia.
The common factor
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These are all fonts that have been the system or UI font in macOS.
I look forward to your putting alternative cases.