With Tony Romo retiring after 14 seasons in the NFL to join the broadcast booth at CBS, now seems like a perfect time to take a look back at his career in Dallas. 

Romo has been a star for so long that it’s easy to forget how his career started. When Romo originally signed with the Cowboys as an undrafted free agent out of Eastern Illinois in 2003, there was a lot of doubt about whether he would even make the roster. 

After sitting on the bench for three seasons, Romo finally got the first start of his Cowboys career midway through the 2006 season. Cowboys coach Bill Parcells had become fed up with Drew Bledsoe, so he decided to turn the offense over to Romo in Week 8. 

Romo wasn’t great in his first start (24 of 26, 270 yards, one touchdown, one interception), but he played well enough to keep the starting job for the following week. 

So when did Romo actually win the job? That came four weeks after his first start and it leads off our list of Romo’s five most memorable moments. 

Thanksgiving coming out party vs. Tampa Bay

When Parcells decided to start Romo for the first time, he made sure there wasn’t a lot of pressure on his quarterback. The Cowboys were on the road for Romo’s first three starts, meaning no one really expected Dallas to win. Despite playing on the road in three straight weeks, Romo and the Cowboys went 2-1. 

Romo then won his fourth start, at home, against the Colts, but the pressure really ramped up when Parcells decided to throw him out in front of a national television audience in a Thanksgiving game against the Buccaneers

“America, meet Tony Romo. Tony, meet America.” 

If any NFL fan in the country didn’t know Romo’s name before that game, they definitely knew it afterward. In one of the best games of his career, Romo threw for 306 yards and five touchdowns, along with no interceptions, in a 38-10 win. 

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Tony Romo had his national coming-out party on Thanksgiving Day in 2006. Getty Images

That game marks one of only two times Romo threw five touchdown passes in his career and the only time where he threw five touchdowns with no interceptions. After Thanksgiving 2006, Cowboys fans were thankful that they finally had their quarterback of the future after sitting through the likes of Quincy Carter, Chad Hutchinson, Vinny Testaverde and Bledsoe following the retirement of Troy Aikman.

Romo would go 6-4 as the Cowboys starter in 2006 in a season that didn’t end until a shocking 21-20 loss to the Seahawks in the wild-card round of the playoffs. That game involved another Romo moment -- can you say botched hold -- however, we’re focusing on the positive here. 

Spinning out of a J.J. Watt sack and throwing a TD

Whenever Romo was being rushed by a defender, the Cowboys quarterback almost always pulled off the same patented move to evade being sacked: The Romo spin. 

Romo pulled off dozens of spins during his career, but the most famous one came in 2014 when he slipped out of J.J. Watt’s grasp to throw a 43-yard touchdown pass.  As you can see below, it looked like Romo was going to get slaughtered by Watt as the Texans defensive end snuck up behind him during this Week 5 game. 

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Tony Romo used his patented spin move on J.J. Watt.  CBS

Instead of getting sacked, Romo spun out and found Terrance Williams with a perfect 43-yard pass that traveled roughly 57 yards through the air (you can see the entire play by clicking here). 

The touchdown pass was huge because it gave the Cowboys a 10-7 third-quarter lead in a game they would win 20-17 in overtime. The Cowboys’ 2014 season ended with a 12-4 record and the team picking up its second playoff win since 1997. The Cowboys might’ve had a team good enough to win the Super Bowl that year, but we’ll never know since the refs decided that Dez didn’t catch that touchdown in the divisional round against the Packers

The 37-yard scramble that went for 4 yards

This might seem like a weird play to have on this list, but it’s the one play in Romo’s career that really showed off how athletic he was, something for which he didn’t always get credit. 

During a 2007 game against the Rams, the Cowboys were facing a third-and-3 at at midfield when something horrible happened: The shotgun snap went over Romo’s head. 

Things got even worse a few second later when Romo accidentally hit the ball with his leg, knocking it back even farther. By the time Romo picked the ball up, he was 33 yards behind the line of scrimmage. 

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Tony Romo somehow turned a 33-yard loss into a first down... with his legs.  Fox

Although this clearly seemed like a disaster in the making, that’s not what happened, thanks to Romo’s athleticism. Even though he was stumbling as he picked up the ball, Romo still managed to get back to the line of scrimmage AND gain 4 yards on the play to give the Cowboys a first down. 

Sure, it only went down as a 4-yard gain in the scorebook, but anyone who watched this play knows that it might’ve been the most impressive 4-yard gain by any quarterback in NFL history. 

Throwing for 506 yards

In what should go down as one of the greatest regular-season games in NFL history, Romo had a career day in a wild 51-48 loss to the Denver Broncos. Earlier on the list, we mentioned that Romo threw five touchdown passes in one game two times in his career. Well, this was the other time. 

In the loss to Denver, Romo threw for 506 yards and five touchdowns. Romo’s passing total was the highest of his career and the 14th highest single-game total in NFL history. Although some fans will remember the interception Romo threw late in the game, it’s important to remember that the Cowboys wouldn’t have even been in this game if not for Romo

With 7:30 left in the third quarter, the Cowboys trailed 35-20 and it looked like the blowout was on. However, thanks to three touchdown passes in an eight-minute period, the Cowboys were able to take a 41-38 lead. The Cowboys gave up 10 points over the game’s final 2:40 in the three-point loss. 

The playoff wins

Although Romo never got the Cowboys to a Super Bowl, he did win two playoff games in Dallas, which is two more playoff wins than any other Cowboys quarterback has had since Aikman. 

In terms of Romo’s career, it’s hard to say which playoff win was bigger. After the 2009 season, Romo led Dallas to a 34-14 blowout victory over the Eagles in the wild-card round, which was huge because it was the Cowboys’ first postseason victory in 13 years. 

Romo threw two touchdown passes during a 27-point second quarter that helped the Cowboys ice the game before halftime. 

The Cowboys’ other playoff win under Romo was the opposite of a blowout: It went down to the wire. 

Following the 2014 season, the Cowboys hosted the Lions in the wild-card round and it looked like they were going to get blown out of the playoffs. With just three minutes to go in the third quarter, the Cowboys trailed 20-7 and didn’t look they were able to get anything going against the Lions’ stingy defense. 

Romo responded by leading three scoring drives over the final 18 minutes. Romo completed the second-half comeback when he hit Terrance Williams for the winning touchdown with just 2:32 left. 

It’s tough to judge Romo by his playoff legacy, because of his four losses -- the Cowboys probably could’ve won three of those. The only playoff loss that came by five or more points was a 34-3 loss to Minnesota following the 2009 season. 

Honorable mention

The speech: Romo’s concession speech, passing the Cowboys’ starting QB job to Dak Prescott, didn’t make the list because we stuck to things that happened on the field, but if we were going to add off-the-field things, then this speech would probably be No. 1. 

“He’s earned the right to be our quarterback,” Romo said of Prescott while rumors were swirling in November. “As hard as that is for me to say, he’s earned that right.”

Romo could’ve made the 2016 season a difficult one for the Cowboys, but instead, he was the perfect teammate even as he watched a younger quarterback steal his job.