Born in Calgary, Alberta on October 2, 1962, Rypien's family moved to the United States when he was three, settling in Spokane, Washington.

He watched from the sidelines as the Redskins won Super Bowl XXII under coach Joe Gibbs in January 1988 behind the quarterbacking of veteran Doug Williams.

[10] Rypien became the second stringer after Jay Schroeder, who lost his job to Williams late in the 1987 season, was traded to the Los Angeles Raiders.

In Week 4 against the newly relocated Phoenix Cardinals, Rypien got his first chance to start for an injured Williams and threw for 303 yards and two touchdowns in a 30–21 loss.

The team missed the playoffs but Rypien received a bid as an injury replacement for Joe Montana and Don Majkowski in that year's Pro Bowl (NFC coach John Robinson elected to bring only one injury replacement for his intended starter and #2 quarterback).

He was named the MVP (Most Valuable Player) of the game, passing for 292 yards and 2 touchdowns and leading his team to a 37–24 win over the Buffalo Bills.

However, the team battled age and injuries and finished the regular season with a 9–7 record, barely making the playoffs.

Although a dominant team performance in the playoffs brought victory over the Minnesota Vikings in an NFC Wild Card away game, the Redskins eventually lost on a rainy, muddy field in a bruising game vs. the San Francisco 49ers, and the Rypien era was essentially over.

Under new head coach Richie Petitbon, Rypien had his best training camp in 1993 and expectations were high following a Monday Night win over the defending Super Bowl Champion Dallas Cowboys.

However, Rypien injured his knee in Week 2 against the Arizona Cardinals[17] and the team began a precipitous slide toward a 4–12 season finish.

[18] When he was healthy enough to return, Rypien performed spot duty, sharing time with the newly acquired Rich Gannon.

[24] His last NFL touchdown pass came in relief of Eagles quarterback Ty Detmer, an 8-yarder to Irving Fryar with five seconds remaining in a 37–10 loss to the Indianapolis Colts.

[30] Rypien's last professional game was on June 10, 2006; as part of a promotional gig for the Rochester Raiders of the Great Lakes Indoor Football League (GLIFL).

[47] Rypien himself confirmed that he has struggled with mental health issues since his retirement from football, even attempting suicide by overdosing on pills before his wife stopped him.