Pearson was born and raised in South River, New Jersey, and began his football career at South River High School as one of the wide receivers of Joe Theismann. As a junior, he succeeded Theismann as the starting quarterback. He also lettered in baseball and basketball, graduating in 1969.
He accepted a football scholarship from the University of Tulsa. He started four games at quarterback as a sophomore. The next year was converted into a wide receiver, registering 22 receptions for 429 yards and 3 touchdowns. As a senior, he led a run-oriented offense with 33 receptions for 690 yards and 5 touchdowns. He finished his college career with 55 receptions for 1,119 yards, 8 touchdowns and a 20.3 yard average per reception.
Pearson received the University's President's Award as the team's "best spirited and most unselfish" member. In 1985, he was inducted into the Tulsa Athletics Hall of Fame.
In 1973, he was signed as an undrafted free agent by the Dallas Cowboys and made the team as a third-team wide receiver because of his special teams play. As a rookie, he was forced to replace Otto Stowe after he suffered a broken ankle in the seventh game of the season against the Philadelphia Eagles, and his backup Mike Montgomery would also fell to injury in the next game. He appeared in 16 games with 6 starts, making 22 receptions for 388 yards and 2 touchdowns.
In 1974, Stowe asked to be traded and Pearson became the full-time starter opposite Golden Richards. He led the team with 62 receptions and 1,087 yards, while also catching 2 touchdowns. He would keep leading the team in receiving until 1978, when Tony Hill took over the number one role at wide receiver.
In 1979, he and Tony Hill—along with Tony Dorsett—helped the Cowboys become the first team in NFL history to have two 1,000-yards wide receivers and a 1,000-yard running back, when he recorded 55 receptions, 1,026 yards and 8 touchdowns. Pearson and Hill also became the first wide receiver tandem in Cowboys history, to record 1,000-yard receiving seasons in the same year.
In 1980, he surpassed Bob Hayes' club mark in receptions and was selected by the Cowboys as their nominee for NFL Man of the Year. In the 1981 NFC Championship Game against the San Francisco 49ers, Pearson almost rendered "The Catch" irrelevant when, in the waning moments of the game, he caught a long pass from Danny White that would've gone for a touchdown and won the game for the Cowboys had 49ers cornerback Eric Wright not made a one-handed tackle, stopping him just outside field-goal range (White fumbled on the next play, thus preserving victory for the 49ers and putting them in Super Bowl XVI).
In 1983, he passed Hayes' as the franchise leader in receiving yards. In March 1984 he fell asleep while driving his Dodge Daytona, causing a crash against a parked tractor-trailer. The accident ended his younger brother’s (Carey Pearson) life and forced him to retire from the liver injury he suffered.
Pearson helped the Cowboys to three Super Bowl appearances and a victory in Super Bowl XII in 1978. He also scored a touchdown in Super Bowl X. Pearson was known as "Mr. Clutch" for his numerous clutch catches in game-winning situations, especially the "Hail Mary" reception from Roger Staubach that sealed the victory in a 1975 playoff game, one of the most famous plays in NFL history. He also caught the game-sealing touchdown in 1973 playoff game against the Los Angeles Rams and the game-winning touchdown pass from reserve quarterback Clint Longley in the 1974 Thanksgiving game against the Washington Redskins. All three of those plays were named among the Top 75 plays in NFL history by NFL Films in 1994. In addition in the 1980 playoff game at Atlanta, Pearson's clutch receptions helped win that game in a comeback by the Cowboys.
He rose to become one of the NFL's greatest wide receivers, earning career records of 489 receptions and 7,822 receiving yards, along with 189 rushing yards, 155 yards returning kickoffs, and 50 touchdowns (48 receiving and two fumble recoveries). Pearson was named one of the Top 20 Pro Football All-Time wide receivers, he was also recognized for his achievements by being named to the NFL 1970s All-Decade Team. However, he is the only offensive player from the First Team to not have been elected into the Pro Football Hall of Fame.
Pearson was named All-Pro three times (1974, 1976–77) All-NFC in 1975 and second Team All-NFC in 1978. In addition, Pearson was a Pro Bowler in 1974, 1976 and 1977. He led the National Football Conference (NFC) in pass receptions in 1976 with 58. He served as offensive captain for the Cowboys in 1977, 1978, 1982 and 1983.
His career accomplishments left such a mark with the Dallas Cowboys, that his number 88 jersey is reserved for the best talent at wide receiver. Hall of Famer Michael Irvin and Dez Bryant have worn it.
In 2009, on the NFL Network show "NFL's Top 10", in the episode titled "Greatest Dallas Cowboys", he is number 10 on the list, although the update in 2016 where Drew was not on the list and was replaced by Randy White as #10 as well.
On August 19, 2011 Cowboys owner Jerry Jones announced that Pearson had been selected for inclusion into the Dallas Cowboys Ring of Honor. Pearson, Charles Haley and Larry Allen were inducted during the half-time show of the Cowboys-Seahawks game on November 6, 2011.
The Professional Football Researchers Association named Pearson to the PRFA Hall of Very Good Class of 2010 Since his retirement in 1983, Pearson has worked extensively as a sports broadcaster for such networks as CBS and HBO; he previously hosted the Dallas Cowboys post-game show.
For three months in early 1986, Pearson worked as the weekend sports anchor at KENS Channel 5 in San Antonio, Texas.
He is also the CEO of Drew Pearson Companies, a manufacturer of licensed headwear since 1985.
Was the Head Coach of the Arena Football League's Dallas Texans during the 1991 season, guiding the team to a 4-6 record.
Was the General Manager of the New York/New Jersey Hitmen during the only season of the XFL. Midway through the season, he began attending games from the sideline and talking with announcers, something head coach Rusty Tillman refused to do.
Pearson is exclusively represented by PPI Marketing for speaking engagements and appearances. Pearson currently lives in Plano, Texas.
Received the NFL Alumni Career Achievement Award in 2005 for his post-NFL career success.
Played basketball with Marques Haynes on a team called Harlem Magicians. Pearson is married to Haynes' daughter.
Pearson wore #88 with the Cowboys. Later, Michael Irvin wore #88 for the Cowboys during his Hall of Fame career, giving the number a special "dual" legacy in club history. When the Cowboys drafted Dez Bryant in the first round of the 2010 NFL draft, they immediately announced that Bryant would wear #88 and Pearson later posed for a photo in a Cowboys uniform with Bryant and Michael Irvin that was part of the 2010 edition of the popular Dave Campbell's Texas Football magazine.
On August 18, 2012 Drew Pearson announced that he will host a new sports and lifestyle talk show titled "The Drew Pearson Show" with co-hosts Paul Salfen, Kristen Keith and Michael Nast.The show is on Fox Sports Southwest Each show has a higher purpose from granting wishes with Make-A-Wish to finding toys for children at Christmas via Toys for Tots Drew Pearson and his Dallas Cowboys"Star Power" help 501C3. The first few local guests included five-time Super Bowl champion Charles Haley, as well as Kool & The Gang's Sir Earl Toon, Machete actor Billy Blair, "Friday Night Lights" star Drew Waters, "American Idol" and "Celebrity Rehab" personality and singer Nikki Mckibbin, 13-time world champion power lifter Amanda Harris (aka Barbie Barbell) and half the cast of Style Network's hit show "Big Rich Texas". Salfen interviewed international stars like Michael Pena and Natalie Martinez for End of Watch and Tim Burton, Winona Ryder and Oscar winner Martin Landau for Frankenweenie and the creators of Sinister, Ruby Sparks and Paranormal Activity 4.
Is a color commentator for the Allen Wranglers of the Indoor Football League.
Served as Honorary Chairman for 2012 Silver Dollar Ball benefiting American Cancer Society
On August 9, 2013, he was a guest on the Alex Jones radio show.
On September 25, 2014, he was a guest on the Norm Hitzges Radio Show.
On April 28, 2017, Pearson was selected to announce a pick at the 2017 NFL Draft, which took place at Philadelphia. Amidst boos, he let out a dramatic speech, and announced Chidobe Awuzie as the 60th pick for the Cowboys.