Cutler was born in Santa Claus, Indiana, in 1983. Cutler attended Heritage Hills High School in Lincoln City, Indiana. He started three years at quarterback for the Patriots football team, amassing a combined 26–1 record in his junior and senior years, including a perfect 15–0 during his senior year. Cutler and his team outscored opponents 746–85, including a 90–0 shutout at Pike Central. During his senior year, Cutler connected on 122 of 202 passes (60.4%) for 2,252 yards with 31 touchdowns, while rushing 65 times for 493 yards with 11 touchdowns. He also started at safety for three years, intercepting nine passes as a senior, 12th overall in the state. His team’s perfect record during his senior year included the school’s first 3A state championship, where Heritage Hills beat Zionsville in overtime, 27–24. The most notable play of the game occurred when Cutler lateraled the ball to the halfback, Cole Seifrig, who then passed it to Cutler who ran it into the end zone. Cutler also played strong safety in the state championship and made 19 tackles.

Cutler’s first win came in his third start on December 17, which was a 37–20 road victory over the Arizona Cardinals. He finished the game 21-of-31 with 261 yards, two touchdowns, an interception and a QB rating of 101.7, the highest for a Broncos rookie since John Elway in 1983. One touchdown traveled 65 yards in the air, and was recorded as a 54-yard touchdown to Javon Walker on the Broncos’ third play of the game. Shanahan said to the media, “You saw what he could do today. It doesn’t take a genius out there to figure out this guy is very composed, can make all the throws and plays with a lot of confidence.”

In Week 10, the 4-5 Broncos faced the 6-3 Tennessee Titans (and fellow 2006 draftee Vince Young for the first time) in a MNF game. Cutler posted a career-second-best 137.0 passer rating in a 34–20 victory. He was the first Broncos quarterback since Elway in 1995 to throw two 40+ yard touchdowns in a game (of the team’s franchise-record four 40+ yard touchdowns that night), and the 5–5 Broncos moved into a tie with San Diego atop the AFC West. However, the Broncos won only one of the next five games, a 41–7 Chiefs blowout. In that game, Cutler passed for four touchdowns and a then-career-best rating of 141.0. But that bright spot came between two pairs of losses; in the four games Cutler had five interceptions, took 12 sacks, twice had a rating under 50.0, and culminated in 23–3 loss to San Diego that eliminated the Broncos from the playoffs. Cutler salvaged a 7–9 record with a 22–19 overtime win over Minnesota, eliminating them as well.

Cutler attended Vanderbilt University in Nashville, Tennessee. He started all 45 career games that he played for the Vanderbilt Commodores football team, the most starts by a quarterback in school history. He did not miss a game in college due to injury. The Commodores were 11–35 during his tenure, including going 5–27 versus the SEC. In 2002, Cutler set the school record for touchdowns and rushing yards by a freshman and rushed for more yards than any other Southeastern Conference quarterback that year. The Associated Press honored him with a first-team freshman All-SEC selection. In 2004, as a junior, Cutler completed 61.0 percent of his passes, setting a school record, while throwing for 1,844 yards with 10 touchdowns and a career-low five interceptions.

The 2005 season, Cutler’s final year of play at Vanderbilt, was his most successful. As an 11-game starter, he completed 273 of 462 passes (59.1%) for 3,073 yards, 21 touchdowns and nine interceptions, as he became the first Commodore to win the SEC Offensive Player of the Year (coaches and media) since 1967. With his senior-season performance, Cutler became the second Commodore to throw for more than 3,000 yards in a season, while his 273 completions and 21 touchdowns ranked second on the school’s single-season list. He led the Commodores to victories over Wake Forest, Arkansas, Ole Miss, Richmond and Tennessee. The Commodores also scored the second most points ever (42) laid upon the Florida Gators at their current home field at Ben Hill Griffin Stadium. Vanderbilt nearly upset the 13th-ranked Gators before falling 49–42 in the second overtime after a controversial excessive celebration call prevented the Commodores from going for 2 at the end of regulation. Reflecting on Cutler’s college career, former Denver Broncos safety John Lynch said, “If this guy can take a bunch of future doctors and lawyers and have them competing against the Florida Gators, this guy is a stud.”

Cutler graduated from Vanderbilt in 2005 with a Bachelor’s degree in human and organizational development.

Cutler was ranked by many experts as the third-best quarterback prospect in the 2006 NFL Draft, after Matt Leinart of USC and Vince Young of Texas. ESPN’s Chris Mortensen and Ron Jaworski tabbed him as the best quarterback available in the draft, and some scouts believed he had better arm strength than Young and Leinart, and compared him to Brett Favre for his gunslinger attitude. At the 2006 NFL Scouting Combine, Cutler completed 23 repetitions of a 225-pound bench press (more than some linemen) and ran a 40-yard dash in 4.77 seconds.

Cutler was selected, with the 11th pick of the first round of the draft, by the Denver Broncos, who traded their 1st and 3rd round picks to the St. Louis Rams to move up. Many believed Cutler was chosen by the Broncos due to the lackluster performance in the previous season’s AFC Championship Game of Jake Plummer. After the pick by Denver, Cutler said, “We had no warning. I think I knew about 15 seconds before everyone else did.” Cutler, as predicted by most, was the third quarterback chosen, after Young (3rd overall) and Leinart (10th). He is the third first-round pick to come from Vanderbilt, preceded by Will Wolford and Bill Wade. On July 27, 2006, Cutler agreed to terms on a six-year $48 million contract, which included $11 million in bonuses.

After a strong training camp in 2006, Cutler was promoted from third to second on the Broncos’ quarterback depth chart ahead of Bradlee Van Pelt. He passed for more yards than any other rookie in the preseason.

The 2007 NFL season marked Cutler’s first full season as the starting quarterback of the Denver Broncos. In the first game of the season against the Buffalo Bills, Cutler led Denver to a comeback win on a 12-play, 42-yard drive culminating in a Jason Elam 42-yard field goal as time expired. Cutler’s pass attempts (39), completions (23), and yards (304) for the game were career-highs at the time. He led Denver to their second straight comeback win the next week in the home opener against the Oakland Raiders. Late in regulation, Cutler moved the team 78 yards in 15 plays for the game-tying field goal with 2:18 remaining. The game went into overtime, where he engineered a 52-yard drive that led to another game-winning field goal by Elam. Cutler had a touchdown pass during the game, making him the first Broncos passer to begin his Broncos career with at least one touchdown pass in his first seven starts. The streak reached nine games through losses to Jacksonville and at Indianapolis (which featured his first career rushing touchdown), but ended with a 41–3 home loss to the San Diego Chargers in the fifth game of the season.

In late 2007, various experts suggested Cutler was the young quarterback most likely to reach the elite status along the lines of Peyton Manning and Tom Brady. Cutler, Brandon Marshall and Tony Scheffler went to Atlanta together to train and work on timing for the 2008 season.

Cutler, along with former Broncos tight end Tony Scheffler and former Broncos backup quarterback Preston Parsons, took part in an episode of Oprah’s Big Give filmed in Denver in 2007. The episode aired on ABC on March 9, 2008.

During the 2007 offseason, Cutler started the Jay Cutler Foundation, which partnered with Mile High United Way’s Youth Success Initiative to help at-risk youth overcome obstacles and graduate from high school.

Before the 2008 regular season began, Cutler and tight end Daniel Graham were voted offensive captains by Broncos teammates.

After the 2008 season, coach Shanahan was fired and replaced by the Patriots’ offensive coordinator Josh McDaniels. On February 28, 2009, ESPN reported that the Broncos were listening to trade offers for Cutler, a possibility he found upsetting. McDaniels denied interest in trades, but Cutler did not believe him. On March 15, Cutler listed his Colorado home for sale, and confirmed that he had officially asked the Broncos to trade him.On March 31, Broncos owner Pat Bowlen announced that the team would accommodate his request, and three days later Cutler was indeed traded with the Broncos’ 2009 fifth-round draft pick to the Chicago Bears for quarterback Kyle Orton, the Bears’ first- and third-round selections in 2009, and first-round pick in 2010. On October 20, Cutler and the Bears came to terms on a two-year contract extension worth $30 million, running through 2013.

On May 1, 2008, Cutler announced that he had been diagnosed with type 1 diabetes and needs daily insulin shots. He is responding well with the insulin treatments.

Cutler finished the season with career-highs in passing completions (384), passing attempts (616), passing yards (4,526), passing touchdowns (25), interceptions (18), rushing attempts (57) and rushing touchdowns (2). At the time, his passing yards, completions and attempts were all single-season franchise records for the Broncos. He also had the most 300-yard passing games (8) in team history. For the season, Cutler ranked third in the NFL in completions (first in the AFC), second in passing attempts (first in the AFC), third in passing yards (first in the AFC) and seventh in passing touchdowns (third in the AFC). He was selected as the FedEx Air Player of the Week for his performances during Weeks 10, 13 and 14. He finished third in fan voting for AFC quarterbacks in the 2009 Pro Bowl, and was officially selected as a reserve. Before the game in Hawaii, fellow Pro Bowlers Peyton Manning, Nick Mangold, and Kris Dielman threw him into a pool, ruining his blood sugar monitor. A replacement one was found at a drugstore, and Cutler played without incident.

For the 2009 season, Cutler teamed up with Eli Lilly and Company in a campaign called “Touchdowns For Diabetes”. For every touchdown pass Cutler threw during the 2009 season, Lilly sent a child to diabetes camp by donating $1,000 to the ADA’s “Camp Scholarship” fund—roughly the cost of providing tuition for one child to attend a week of diabetes camp. For every pass Cutler completed in 2009, Lilly donated $100 to the ADA Camp Scholarship fund to allow even more kids the chance to attend camp the following summer.

Cutler began dating reality television star Kristin Cavallari in Fall 2010 and became engaged to her in April 2011. They called off the engagement in July 2011, but subsequently confirmed their reconciliation that November. Cutler and Cavallari married on June 7, 2013 in Nashville, Tennessee. They have two sons and one daughter: Camden Jack (born August 8, 2012), Jaxon Wyatt (born May 7, 2014), and Saylor James (born November 23, 2015). Despite the birth of his first son coming the day before the Bears played their preseason opener against the Denver Broncos, Cutler dressed for the game, though he did not play.

Throughout 2011, offensive coordinator Mike Martz was commonly criticized for aggressive play-calling in a pass-happy offense, leading to unnecessary wear on a quarterback returning from injury. In the season opener against the Atlanta Falcons, Cutler started the season off on a good note with 312 passing yards, two touchdowns, and one interception in the 30–12 win. In Week 2 against the New Orleans Saints, Cutler was sacked 6 times and kicked in the throat. During Week 6, Cutler was caught on microphone asking a player to go to Martz on the sideline, and “tell him I said fuck him!” Despite these incidents, by Week 10, Cutler had a middle-of-the-pack QB rating of 85.7 (12th in the league) and the Bears were 6–3. However, on November 20, Cutler broke the thumb on his throwing hand tackling San Diego’s Antoine Cason after an interception. He played through the final drive for the win, but the injury required season-ending surgery. Under backups Caleb Hanie and Josh McCown, the Bears lost six of their remaining seven games, and missed the playoffs. Overall, in his shortened 2011 season, Cutler had 2,319 passing yards, 13 touchdowns, and seven interceptions.

In 2011, after the Bears lost five straight games while Cutler was out with a thumb injury, Chicago recording artist Magic 1 recorded “Cutty Come Back”, a parody of the song “Baby Come Back”.

Cutler supported Mitt Romney in the 2012 presidential election, and Donald Trump in 2016 and 2020.

In 2012, Cutler visited Perspectives Charter School in Chicago, and talked about diabetes awareness.

In 2013, Cutler played himself in an episode of the comedy show The League, alongside his wife, Kristin Cavallari, who appeared in one other episode of the show.

On January 2, 2014, Cutler signed a seven-year deal, keeping him with the Bears through the 2020 NFL season.

An internet meme, called “Smokin’ Jay Cutler”, portrays pictures of Cutler in an apathetic state with a cigarette photoshopped into his mouth. Cutler commented he is aware of the meme and “gets a kick out of that”. Aaron Rodgers of the Green Bay Packers performed a smoking gesture to reference the meme during a 38–14 win over the Bears in 2014.

With Adam Gase’s departure to become the head coach of the Miami Dolphins, Dowell Loggains became the Bears’ offensive coordinator. In Cutler’s first two games, he was sacked 8 times and had two interceptions in losses to the Houston Texans (where he injured his right thumb but completed the game), and Philadelphia Eagles (where he re-aggravated his injury and was replaced by Brian Hoyer). He missed the next five games before making his return against the Vikings, where he completed 20 of 31 passes for 252 yards, a touchdown and a 100.5 passer rating en route to a 20–10 victory. Zach Miller praised Cutler’s performance in his return, even adding that he delivered a half-time speech to motivate his teammates. Cutler fumbled and threw two interceptions (including a pick-6) in a loss to Tampa Bay. Cutler sustained a labrum injury in his throwing shoulder on November 20, 2016 in a loss to the Giants, and missed the rest of the season. In his five games in 2016, Cutler recorded 1,059 passing yards, four touchdowns, five interceptions, and a 78.1 passer rating.

On March 9, 2017, Cutler was released by the Bears through a $2 million buyout clause, after the guaranteed years in his seven-year contract had run out. After Cutler’s lackluster performances and injuries, the move had been expected for months, as the Bears had decided to award a $45 million contract to Mike Glennon. In May 2017, Cutler announced his retirement from professional football and was hired by Fox Sports to be a commentator.

On August 3, 2017, Miami Dolphins quarterback Ryan Tannehill suffered a season-ending injury, and the team reached out to the retired Cutler. On August 7, Cutler signed a one-year, $10 million contract with the Dolphins, reuniting him with former Bears offensive coordinator Adam Gase, who had been hired as Miami’s head coach in 2016.

On December 27, he said he would probably only continue his NFL career if he can be a starter, stating “I wouldn’t want to move again or go somewhere just to back up.” He started 14 games and finished with 2,666 passing yards, 19 touchdowns, and 14 interceptions for the Dolphins in the 2017 season. The Dolphins did not make the playoffs and Cutler went 6–8 as a starter. Many teammates, including receiver Kenny Stills, praised Cutler during the season; Stills described him as “a good man. People in other places have kind of given him a hard time. I got to know him as a man and as a player and I appreciate him. I like him. I’m thankful for the experience of playing with him, catching some balls from him.”

In April 2020 the couple announced that they are getting a divorce, with Cavallari saying the split came as the result of the two simply “growing apart.”