Michael Phelps' bid for his fifth gold medal of Rio's Summer Olympics came up short, as he couldn't catch Singapore's Joseph Schooling in the 100-meter butterfly Friday. Schooling also broke Phelps' Olympic record.

For Phelps, this was the first event of these games in which he's failed to win a gold medal. And at 31 years old, he watched Schooling, 21, touch the wall first at 50.39 — breaking Phelps' Olympic mark of 50.58 that he set at the 2008 Beijing Games. For Singapore, it was also the country's first gold medal ever.

In her race that followed Phelps', Katie Ledecky did exactly what the swimming world has come to expect her to do, winning the women's 800-meter freestyle by several body lengths. She also set a new world record of 8:04.79 in the event.

By midway through the race, Ledecky was well ahead of the world-record pace. The only question was how far ahead of her own mark she would finish — and the answer was by nearly two seconds. She broke the world record of 8:06.68 that she set in January, and also shattered her own Olympic record of 8:12.86, a time she clocked in a qualifying heat yesterday.

Ledecky is now finished with her events in Rio. Taking silver behind her in the 800m free was Canada's Jazz Carlin; the bronze went to Boglarka Kapas of Hungary.

Both Ledecky's and Phelps' races came after a contest that saw the continuing breakthrough of American Maya DiRado, who won gold in the women's 200-meter backstroke at the Olympic Aquatics Stadium in Barra's Olympic Park.

DiRado beat out another star of these games — Hungary's Katinka Hosszu — at the wall after taking the lead in the closing lengths. DiRado's time of 2:05.99 beat Hosszu by just 0.06 seconds. Canada's Hilary Caldwell won the bronze medal.

For Team USA, the gold didn't stop flowing there. In the men's 50-meter freestyle, the last final of the night, Anthony Ervin won in 21.40, edging France's Florent Manaudou (21.41) and his American teammate Nathan Adrian (21.49) in the one-length sprint.

At age 35, Ervin now becomes the oldest swimmer to win an individual gold at the Olympics. You might recall that Michael Phelps, 31, claimed that record just this week.

Ervin won gold in this same event 16 years ago — and he made headlines for selling that medal for $17,000 back in 2004, when he donated the proceeds to UNICEF to help relief efforts in tsunami-stricken Indonesia.

After his race, Ervin slapped the water — hard — with a heavily tattooed arm. It was an understandable reaction for a swimmer who retired at age 22, took around eight years off from competitive swimming, and then came back.

We'll note that when Ervin won the 50m free in Sydney 16 years ago, he did so in a time of 21.98 (in a golden tie with training partner Gary Hall Jr.). In tonight's race, he was faster by 0.58 seconds.

These are supposed to be the last Olympic Games for Phelps, who also retired and came back after more than a year off.

This was Phelps' last individual event at the Rio Summer Olympics, and another chance for an individual win over Chad le Clos of South Africa, the swimmer who took an Olympic gold medal in front of him in the 200-meter butterfly at the 2012 London Games.

Instead of beating him, Phelps tied le Clos at 51.14. Their tie also included Laszlo Cseh of Hungary — meaning that this race has three silver medalists.

In a show of sportsmanship and solidarity, Phelps, le Clos, and Cseh — standing in that order — held hands and took the podium together for their medal ceremony.

If Phelps was disappointed with his non-gold medal, it did not show. Laughing and talking with le Clos and Cseh, he flashed a smile as he held up his silver medal. Then he and the other swimmers took the to step to join Schooling and pose for a photo: three silver medalists, one gold winner, and no bronze in sight.

For Phelps, it's Olympic medal number 27 — and his third silver.

Copyright 2016 NPR. To see more, visit NPR.

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