Jamie Weeks was born on March 13, 1959, in Nurnburg, West Germany, while his father was stationed there in the U.S. Army. He enlisted in the U.S. Army on September 17, 1980, and completed basic training at Fort Leonard Wood, Missouri, in November 1980. SP5 Weeks next attended Air Traffic Control Radar Operator School at Fort Rucker, Alabama, from November 1980 to May 1981, followed by service as an Air Traffic Controller at Fort Campbell, Kentucky, from May 1981 until he was selected for Warrant Officer Candidate School in January 1983. After completing the Warrant Officer Rotary Wing Aviator Course, he was appointed a Warrant Officer in the U.S. Army and designated an Army Aviator on November 8, 1983. WO Weeks next attended AH-1S Cobra transition training from November 1983 to January 1984, followed by service as an AH-1 pilot with the 4th Aviation Battalion at Fort Hood, Texas, from February 1984 to October 1986. CW2 Weeks served as an AH-1 pilot with the 7th Attack Reconnaissance Squadron at Camp Stanley, South Korea, from October 1986 to April 1988, and then as an AH-64 Apache pilot and instructor pilot with Company C, 1st Battalion of the 101st Aviation Regiment at Fort Campbell from April 1988 to December 1993. During this time he deployed to Dhahran, Saudi Arabia, in support of Operation Desert Shield from August to December 1990. CW5 Weeks next served as an A/MH-6 Little Bird pilot with Company B, 1st Battalion of the 160th Special Operations Aviation Regiment (Airborne) at Fort Campbell from December 1993 until he was killed in action in Iraq when the MH-6 he was piloting was shot down on May 14, 2006. During this time he deployed to Haiti in support of Operation Uphold Democracy in 1994, to Afghanistan in support of Operation Enduring Freedom multiple times between 2001 and 2006, and to Iraq in support of Operation Iraqi Freedom multiple times between 2003 and 2006. Chief Warrant Officer Weeks was buried at Resthaven Memorial Gardens in Clarksville, Tennessee.

His Silver Star Citation reads:

For Gallantry in action on 14 May 2006, while serving as an AH-6 Pilot operating against an entrenched enemy force during a daylight raid in support of Operation Iraqi Freedom. Chief Warrant Officer Five Weeks continued to make successive assaults in support of the ground forces, without regard for his own personal safety, until his aircraft was shot down. His actions destroyed several enemy positions, enabling the ground forces to consolidate into defensive positions. Without Chief Warrant Officer Five Weeks' courage and gallantry under hostile fire, the ground forces would have sustained significant casualties. He directly contributed to the successful execution of this direct action mission. Chief Warrant Officer Five Weeks' distinctive accomplishments are in keeping with the finest traditions of military service and reflect great credit upon himself, this Command, and the United States Army.