Gordon has completed three career Grand Slams and has won a total of sixteen Crown Jewel races (three Daytona 500s, four Talladega 500s, three Coca-Cola 600s, and six Southern 500s), both of which are all-time records.

GEM only survived one year as Evernham left Hendrick Motorsports, citing tension between him and the team,[30] ending one of the most dominant driver/crew-chief combinations in NASCAR history.

Gordon extended his Busch experiment one more year, through 2000 as co-owner, with Rick Hendrick buying Evernham's half, and GEM becoming JG Motorsports.

However, during the season, many doubted Gordon's ability to compete at such a level at such a young age because of his tendency to push the cars too hard and crash.

[45] He won his fifth pole of the season at Charlotte, but after the race, NASCAR officials found unapproved wheel hubs on his car, and fined the team $60,000 while placing Ray Evernham on probation indefinitely.

[50] At Charlotte, Gordon won The Winston in a Jurassic Park: The Ride scheme; the car was modified by Evernham with assistance from Hendrick chassis engineer Rex Stump, and after the race it was banned following complaints from other team owners.

He finished the season with 10 victories (Daytona, Rockingham, Bristol, Martinsville, Charlotte, Pocono, California, Watkins Glen, Darlington, and New Hampshire).

The following year, Gordon won a modern-era record 13 races at Charlotte, Sonoma, Pocono, Indianapolis, Watkins Glen, Michigan, New Hampshire, Darlington, Daytona, Rockingham and Atlanta.

[78] At Talladega, he recorded his 77th career Nextel Cup victory, to the dismay of the fans, who began throwing beer cans at Gordon's car.

[81] In the three-year timespan, Gordon recorded six total poles, including four in 2008, and a third-place points finish in 2009 behind HMS teammates Mark Martin and champion Johnson.

[90] In the 2012 Budweiser Shootout at Daytona on February 18, Gordon was involved in a crash with two laps to go, rolling his car after a collision with Kurt Busch and Jamie McMurray.

[92] At Richmond, despite troubles early in the race that mired him a lap down, Gordon rallied to finish second to Clint Bowyer, and made his eighth Chase for the Sprint Cup.

[127] Gordon has participated in the Race of Champions three times, including a Nations Cup-winning drive with Team USA's Jimmie Johnson and Colin Edwards at the 2002 event in Gran Canaria.

[131] In 2005, Gordon competed in the Race of Champions event again, this time held in Paris, France, where he was partnered with motocross racer/X Games winner Travis Pastrana.

[132] In 1999, sports columnist Mike Bianchi remarked on Gordon's success at Daytona International Speedway: "The only reason he hasn't won the Rolex 24 is because he's never raced in it.

[146] When Gordon made the decision to step back from full-time driving at the conclusion of the 2015 Sprint Cup Series season, he reportedly put out feelers to television networks about the possibility of joining the broadcast booth.

[153][154] On April 10, 2015, Gordon made his broadcasting debut on Fox Sports 1 during the network's coverage of the O'Reilly Auto Parts 300 at Texas Motor Speedway.

[155] Gordon returned to the broadcast booth for the Drive to Stop Diabetes 300 at Bristol Motor Speedway on April 18,[156] and the Winn-Dixie 300 at Talladega Superspeedway on May 2.

[157] Gordon was one of five active NASCAR drivers to serve as a guest analyst for Fox Sports during the 2015 Xfinity Series season; the other four were Kevin Harvick,[158] Brad Keselowski,[159] Clint Bowyer,[160] and Danica Patrick.

[162][163] Gordon was paired with Mike Joy and Darrell Waltrip in the broadcast booth, replacing Larry McReynolds,[164] who moved to the Hollywood Hotel.

[165] On November 6, 2015, Gordon joined Joy and Waltrip in the booth for the first time at a dress rehearsal during the WinStar World Casino & Resort 350 at Texas Motor Speedway.

[183] Sealey's role as Miss Winston concluded following the 1993 season, and the couple publicly revealed their relationship after the NASCAR awards banquet in December.

[188][189] In court papers, she asked for "exclusive use of the couple's oceanfront home, valued at $9 million, as well as alimony, two cars and periodic use of their boats and an airplane.

[196][197] Gordon had Scott Pruett assigned as a standby driver for Watkins Glen because his wife was due to give birth the weekend of August 8, 2010.

[200] In 2007, Gordon, along with Andre Agassi, Muhammad Ali, Lance Armstrong, Warrick Dunn, Mia Hamm, Tony Hawk, Andrea Jaeger, Jackie Joyner-Kersee, Mario Lemieux, Alonzo Mourning, and Cal Ripken Jr. founded Athletes for Hope, a charitable organization which helps professional athletes get involved in charitable causes and inspires millions of non-athletes to volunteer and support the community.

[212][213] In October 2005, Gordon started a line of wine with Briggs & Sons Winemaking, Co., debuting with a 2004 Carneros Chardonnay, followed by Merlot and Cabernet Sauvignon in January 2007.

[214][215] Eventually, the 2007 Ella Sofia Napa Valley Joie de Vivre won double gold medals at the 2011 Indy International Wine Competition.

[291] In 2014, Gordon joined former F1 driver Michael Schumacher as the only two racers to earn five victories at Indianapolis Motor Speedway in a single racing series.

[292] Since making his Cup Series debut in the Hooters 500 at Atlanta Motor Speedway on November 15, 1992, Gordon never missed a race spanning over 24 consecutive seasons.

In 2010, Gordon similarly asked road course ringer Scott Pruett to be on standby for him at Watkins Glen due to the impending birth of his second child.