Hellestrae was born in Phoenix, Arizona, as a descendant of Norwegian immigrants; his first name Dale is the name of the area his ancestors came from, and his second name Hellestrae is his ancestors' farm's name. He attended Saguaro High School, where he was an All-state selection in football and basketball as a senior. After graduation, he spent one year at the Marine Military Academy. He accepted a football scholarship from Southern Methodist University, where he was a two-year starter at offensive tackle and earned All-Southwest Conference honors as a senior, while playing offensive tackle.
Professional career
Buffalo Bills
Hellestrae was selected by the Buffalo Bills in the fourth round of the 1985 NFL Draft. He was also selected by the Houston Gamblers in the 1985 USFL Territorial Draft. As a rookie, he missed the last 12 games with a broken thumb. In 1986, he played in the first 2 games before missing the next 8 with a broken wrist. In 1987, he was lost for the season after being placed on the injured reserve list with a hip injury. In 1988, he had his only career starts, when he started at right guard in the final two regular season games and in two playoff games. During his four seasons with the team, he could only play in 28 games because of injury problems.
The Dallas Cowboys acquired him with the intention of concentrating on playing long snapper in all of the special teams units and to back up the guard and center positions. During his time with the team he quickly became one of the best long snappers in the NFL and in team history. In 1992, he had 6 special teams tackles. In 1993, he had 7 special teams tackles. In 1994, he had 5 special teams tackles. In 1997, he had 5 special teams tackles. In 1998, he had 9 special teams tackles. In 1999, he had 10 special teams tackles. In the 1990s, the Cowboys organization felt they could find placekickers and punters through free agency, without the need of paying a premium and adversely impacting the salary cap, so they allowed talented and productive players to leave, instead of signing them into long-term contracts. In his 11 seasons playing with the Cowboys, Hellestrae had to snap for eight different placekickers and seven punters, while helping the team win 3 Super Bowls. On March 1, 2001, he was released because of salary cap implications.< At the time he was second in franchise history with 176 consecutive games played, behind Bob Lilly.
Baltimore Ravens
On January 3, 2002, he was signed by the Baltimore Ravens as a free agent to fill in for injured rookie Joe Maese. He played in one regular season game and in two playoff games. He wasn't re-signed at the end of the season.
Personal life
Hellestrae works as a color analyst on professional and NCAA football games, particularly for College Football on Versus. He is also the co-host of Jacobs and Helly in the Morning on 1580AM/99.3FM/95.9FM The Fanatic on Mon-Fri mornings. He is also the color analyst for Arizona Rattlers and High School Football on Cox7. He appears as a guest analyst on "Sports Tonight" on KPNX, Channel 12, in Phoenix with co-hosts Kevin Hunt and Bruce Cooper. He is the owner of Cookies By Design, in the Scottsdale area.