(CNN) If there was a record for breaking records, Michael Phelps would doubtless don his goggles and cap to swim for it.
But the "Baltimore Bullet" couldn't add to his unparalleled 23 Olympic gold medals in the 100-meter butterfly Friday as he was beaten by outsider Joseph Schooling.
Schooling became the first Singaporean athlete to win a Games gold -- and did so in an Olympic record time of 50.39 seconds.
Remarkably Phelps finished in a three-way tie for the silver -- the 27th medal of his career -- along with South Africa's Chad le Clos and Laszlo Cseh of Hungary, as they all clocked the same time of 51.14 seconds.
The 21-year-old Schooling punched the water upon realizing he had foiled three of the biggest names in world swimming.
Phelps will now have to wait to see if he can add to his 23 gold medals when he is expected to take part in Saturday's men's 4x100m freestyle medley.
READ: The other Phelps winning in Rio
Remarkably, Phelps' silver success was about the most downbeat moment on a night of triumph in the pool for Team USA.
Teenager Katie Ledecky picked up a fourth gold medal of the Rio Games in the 800m freestyle final, smashing her own world record in the process to clock a time of eight minutes 04.79 seconds.
She won her first Olympic gold in London four years ago when she was just 15. At such a tender age, it's far from an impossibility that she could could challenge Phelps record in the future.
Ledecky's Friday triumph also means she becomes the first swimmer to win the 200m, 400m and 800m freestyle titles in the same Games since Debbie Meyer did so in Mexico 1968.
Earlier, US teammate Maya Dirado earned her first gold of the Rio Games, after claiming a silver and bronze earlier in the week, as she pipped Katinka Hosszu in the women's 200m backstroke.
Dirado hunted down favorite Hosszu in the final 50 meters, touching the wall fractions of a second before her opponent in the next lane to deny Hungary's "Iron Lady" her fourth gold medal of Rio 2016.
Even more delight was to follow for the US as Anthony Ervin became the oldest Olympic swimming champion with gold in the men's 50m freestyle.
The 35-year-old beat second-placed Florian Manadou of France by a margin of just 0.01 seconds.
Fellow American Nathan Adrian claimed bronze a further 0.07 seconds back.