Assuming you're talking about individuals rather than countries, I've done a fair bit of research into this question.
Because of the spacing of the Olympics every 4 years, it's difficult for athletes in many events to make repeated appearances at the games due to falling from their peak athletic performance. There are many instances of athletes appearing in 3 consecutive Olympics in the same event and winning a medal, but it's harder to find examples of athletes medalling in the same event in 4 or more consecutive games.
That being said, let me introduce you to a fencer named Aladár Gerevich. Early on when I was researching this question I was convinced it would be a multi-way tie between athletes who'd medalled in an event 4 times, until I saw this impressive Olympic résumé:
Gold 1932 Los Angeles Sabre team
Gold 1936 Berlin Sabre team
Bronze 1936 Berlin Sabre individual
Gold 1948 London Sabre team
Gold 1948 London Sabre individual
Gold 1952 Helsinki Sabre team
Silver 1952 Helsinki Sabre individual
Bronze 1952 Helsinki Foil team
Gold 1956 Melbourne Sabre team
Gold 1960 Rome Sabre team
Gerevich is confirmed to be the only Olympian who's medalled in the same event in six different Olympic events: Sabre Team, at the games of 1932, 1936, 1948, 1952, 1956 and 1960. Also of note: all six of these medals were Gold.
For more:
http://en.wikipedia.org/wiki/Alad%C3%A1r_Gerevich
5 medals in the same event:
Edoardo Mangiarotti, Italy
Team Epée
1936 (Gold), 1948 (Silver), 1952 (Gold), 1956 (Gold), 1960 (Gold).
(Not to mention his 4 medals in different years for Team Foil)
Reiner Klimke, Germany
Equestion - Dressage
1964 (Gold), 1968 (Gold), 1976 (Gold), 1984 (Gold), 1988 (Gold)
Pál Kovács, Hungary
Team Sabre
1936 (Gold), 1948 (Gold), 1952 (Gold), 1956 (Gold), 1960 (Gold)
(Well, go figure, he was on the same Sabre team as Gerevich up there, the only difference being that he wasn't around for the 1932 games)
A few notable 4-time event medallists:
Carl Lewis, USA
Long Jump
1984 (Gold), 1988 (Gold), 1992 (Gold), 1996 (Gold)
(Note: He had a shot at 5 straight, as he was 5th in world rankings at long jump in 1980, when the US boycotted the Moscow games)
Jenny Thompson, USA
4 x 100 m Freestyle Relay
1992 (Gold), 1996 (Gold), 2000 (Gold), 2004 (Silver)
4 x 100 m Medley Relay
1992 (Gold), 1996 (Gold), 2000 (Gold), 2004 (Silver)
Birgit Fischer, East Germany / Germany
Kayaking - 500m K4
1988 (Gold), 1992 (Silver), 1992 (Gold), 1996 (Gold), 2004 (Gold)
(Note: This is among 10 medals won in 4 different events at a record 6 different Olympic games, and excludes very real medal chances due to the Eastern Bloc boycott of the 1984 games)
Gert Fredriksson, Sweden
Kayaking - 1000m K1
1948 (Gold), 1952 (Gold), 1956 (Gold), 1960 (Bronze)
Addendum: Al Oerter is the only athlete to win the gold medal in the same event four consecutive times. He won the discus event in 1956, 1960, 1964, and 1968.
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