The team with the most losing seasons in modern era NFL (since the Super Bowl) are the Tampa Bay Buccaneers, who lost 14 season in a row from 1983 to 1996. In 1996, Tony Dungy was hired as head coach of the Bucs, Warren Sapp, Derrick Brooks and Warrick Dunn were drafted and the team made the playoffs in the 97 season with a 10-6 record. The Bucs are also the only team to lose every game in a season. They went 0-14 when the team started in 1976. Since then, the season has expaned to 16 games.
The New Orleans Saints were winless in 20 seasons from 1967 (where the franchise started) up and till the 1986 season. They did however have two 8-8 seasons (1973, 1983) and therefore they are not "winless".
Eagles were winless for 11 seasons (1967-1977).
Lastly there is the Detroit Lions who went 0-16
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Arizona Cardinals, with an astonishing 57 losing seasons (including strike years and pre-Superbowl seasons). That is over 64% of their seasons.
They have had 5 seasons where their record was .500, and just 27 seasons of their 89 in existence where they have posted a winning record (excluding 2009, which they will finish with a winning record).
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Dallas Cowboys (1966-1985).
The New Orleans Saints.