List of high school students who have run a four-minute mile
Sub-four-minute mile runs by U.S. high school students

Name
Time
Date
Venue
Location
Jim Ryun
3:59.0
June 5, 1964
Compton Invitational
Los Angeles, California
Jim Ryun
3:55.3
June 27, 1965
AAU Track and Field Championships
San Diego, California
Tim Danielson
3:59.4
June 11, 1966
San Diego Invitational
San Diego, California
Marty Liquori
3:59.8
June 23, 1967
AAU Track and Field Championships
Bakersfield, California
Alan Webb
3:59.86 (indoors)
January 20, 2001
New Balance Games
New York City, New York
Alan Webb
3:53.43
May 27, 2001
Prefontaine Classic
Eugene, Oregon
Lukas Verzbicas
3:59.71
June 11, 2011
Adidas Grand Prix
New York City, New York
Matthew Maton
3:59.38
May 8, 2015
Oregon Twilight Meet
Eugene, Oregon
Grant Fisher
3:59.38
June 4, 2015
Festival of Miles
St. Louis, Missouri
Drew Hunter
3:58.25 (indoors)
February 6, 2016
Armory Track Invitational
New York City, New York
Michael Slagowski
3:59.53
April 29, 2016
Jesuit Twilight Invitational
Portland, Oregon
Reed Brown
3:59.30
June 1, 2017
Festival of Miles
St. Louis, Missouri

Question: Who was the first person to break Jim Ryun's mile record, and when and where did it take place?
Answer: Alan Webb broke Ryun's 36-year old mile record (3:55.3), running 3:53.43 at the Prefontaine Classic in 2001.