Kobayashi's father owns a sushi restaurant. He began competing in karting in 1996, aged nine, finishing third in his first season in the SL Takarazuka Tournament Cadet Class. Over seven years he took four karting titles, including two wins in the Toyota SL All Japan Tournament Cadet Class.
In 2004, Kobayashi signed for Toyota's Driver Academy and began open-wheel racing in Formula Renault, entering the Asian, German, Italian, and Dutch championships and taking two race victories in the Italian championship. He then won both the Italian and European Formula Renault championships with six wins apiece.
In 2006, Kobayashi entered the Formula 3 Euro Series with ASM Formule 3 alongside Paul di Resta, Giedo van der Garde, and Sebastian Vettel. He took three podiums in his debut season, finishing eighth in the Drivers' Championship and first in the Rookie's Championship. He also entered the Macau Grand Prix, qualifying on pole but finishing 19th, and the Masters of Formula 3, where he started tenth and finished eleventh.
At the start of 2007, Kobayashi was named one of Toyota's Formula One test drivers alongside Kōhei Hirate. He remained in the Formula 3 Euro Series and achieved his first Formula 3 win at Magny-Cours, a support race for the French Grand Prix, finishing fourth in the Drivers' Championship.
Following a strong GP2 Asia Series campaign in early 2008, Kobayashi won his first GP2 Series race in only the second race of the season. Starting from pole in the sprint race at Circuit de Catalunya, he took victory after a drive-through penalty was handed to Romain Grosjean for moving more than once to defend position under a safety car period. Kobayashi finished the season sixteenth. He won the GP2 Asia Series the following winter, winning two races, before finishing sixteenth again in the 2009 main series.
On 16 November 2007, Kobayashi was confirmed as Toyota's third driver in place of the departing Franck Montagny, serving as test and reserve driver during the 2008 and 2009 seasons.
At the 2009 Japanese Grand Prix, Kobayashi ran in free practice in place of Timo Glock, who was ill. Glock crashed in qualifying and was unable to race; the FIA refused Toyota's request to run Kobayashi as he had not participated in a Saturday session.
Kobayashi made his Formula One race debut at the 2009 Brazilian Grand Prix following a complication to Glock's injury. He qualified eleventh in a rain-affected session red-flagged twice and finished tenth, later promoted to ninth after Heikki Kovalainen was penalised. While running sixth, he held off Jenson Button for several laps; Button, who needed to finish well to clinch the championship, described Kobayashi as "absolutely crazy, very aggressive." At the 2009 Abu Dhabi Grand Prix — the inaugural day-night race — Kobayashi qualified twelfth and finished sixth, scoring his first World Championship points. Before Toyota withdrew from Formula One, Kobayashi had been expected to receive a full-time seat for 2010.
Following Toyota's withdrawal, Kobayashi was confirmed on 17 December 2009 to drive for Sauber for 2010, the team still named BMW Sauber despite having been sold back to founder Peter Sauber. His teammate was former McLaren tester Pedro de la Rosa.
During the 2010 Australian Grand Prix, a front wing failure caused Kobayashi to hit the barrier, triggering a three-car crash involving Nico Hülkenberg and Sébastien Buemi. In China he was involved in a three-way collision with Buemi and Vitantonio Liuzzi on lap one, making him the only driver to retire from the first four races. In Turkey he scored his first 2010 points, finishing tenth. In Valencia he finished seventh after overtaking both Fernando Alonso and Sébastien Buemi in the final laps on fresh tyres after running the majority of the race third on his first set. He followed that with sixth in Silverstone, eleventh in Germany, ninth in Hungary, and eighth in Belgium. At the Italian Grand Prix he suffered a gearbox failure and retired from Singapore after hitting a barrier. His teammate changed in Singapore with Pedro de la Rosa removed in favour of Nick Heidfeld. In Japan, Kobayashi qualified fourteenth and finished seventh. He finished eighth in Korea and tenth in Brazil, ending the season with 32 points. Murray Walker stated Kobayashi was "without a doubt Japan's best [F1 driver] yet." Martin Brundle described his overtaking technique: "He gets to the normal braking point and then goes, 'Now, which one is the brake again? That's right, it's on the left,' and he just sails past people!" He outqualified de la Rosa and Heidfeld eleven times to eight over the season.
In 2011, Kobayashi remained at Sauber (renamed from BMW Sauber to Sauber F1 Team), partnered by GP2 graduate Sergio Pérez. Kobayashi and Pérez were both disqualified from the Australian Grand Prix after a rear-wing irregularity. In the Canadian Grand Prix, Kobayashi worked his way from thirteenth to second before the red flag, but tyre changes after the restart dropped him, and a spin while lapping a backmarker and being rear-ended by Nick Heidfeld cost him further. He finished seventh, 0.045 seconds behind Felipe Massa, who passed him on the final straight. His season best was fifth at Monaco.
On 28 July 2011, Kobayashi was confirmed at Sauber for 2012 alongside Pérez. He started the 2012 season with sixth at the Australian Grand Prix. At the Chinese Grand Prix he started third behind the Mercedes of Nico Rosberg and Michael Schumacher, dropping to tenth but setting fastest lap. At the German Grand Prix he finished fourth on-road but was classified fourth after a post-race penalty for second-placed Sebastian Vettel. He qualified a career-best second for the Belgian Grand Prix but was caught in a first-corner accident with four other drivers, being the only one of the five to continue and finishing thirteenth.
Kobayashi took his maiden Formula One podium with third place at the Japanese Grand Prix, holding off Button throughout the race. He became the first Japanese driver to finish on a Formula One podium in Japan in 22 years, after Aguri Suzuki in the 1990 Japanese Grand Prix, and was the third Japanese driver to finish on a Formula One podium after Suzuki and Takuma Satō in the 2004 United States Grand Prix. On 23 November 2012, Sauber announced Kobayashi would not continue for 2013, with Nico Hülkenberg and Esteban Gutiérrez forming the race team. Despite raising around €8 million in sponsorship, Kobayashi chose to seek a more competitive drive for 2014 rather than race in 2013. He finished twelfth in the 2012 Drivers' Championship with sixty points.
On 11 March 2013, Kobayashi was confirmed to drive for AF Corse in the 2013 FIA World Endurance Championship in the LMGTE-Pro class in a Ferrari 458 GT. At the 81st 24 Hours of Le Mans, alongside Olivier Beretta and Toni Vilander, their Ferrari covered 312 laps, finishing fifth in the GTE-Pro class. The race was run in difficult weather conditions with a record twelve safety car periods.
On 21 January 2014, Kobayashi was confirmed to return to Formula One with Caterham alongside Marcus Ericsson. At the Australian Grand Prix he crashed into Massa at the start due to a brake failure. In Malaysia he ran as high as eighth before finishing thirteenth. On 20 August 2014, German driver André Lotterer replaced Kobayashi for the Belgian Grand Prix. Kobayashi returned at the Italian Grand Prix after Lotterer declined further appearances when reserve driver Roberto Merhi attempted to qualify for a Super Licence in practice.
On 4 February 2016, Kobayashi was confirmed as a LMP1 driver for Toyota Gazoo Racing in the FIA World Endurance Championship. He scored his first WEC race victory at the 2016 6 Hours of Fuji. In 2017 he set the current lap record at the Circuit de la Sarthe with a time of 3:14.791.
Kobayashi won the FIA World Endurance Championship alongside Mike Conway and José María López in the 2019–20 season and in 2021. He won the 2021 24 Hours of Le Mans from pole alongside Conway and López. He is the fourth Japanese driver to win Le Mans and only the second to do so for a Japanese manufacturer, after Masanori Sekiya.
In December 2021, Toyota announced Kobayashi would succeed Hisatake Murata as team principal of the manufacturer's WEC programme, combining that management role with his duties as a driver.
On 7 June 2023, Kobayashi was announced to make his NASCAR Cup Series debut driving the No. 67 Toyota Camry for 23XI Racing at the Indianapolis Motor Speedway road course, finishing 33rd. In 2024, he returned to NASCAR for 23XI Racing at Circuit of the Americas, finishing 29th in the 2024 EchoPark Automotive Grand Prix.
Kobayashi drove for Team LeMans in the 2015 Super Formula season, scoring three podiums and finishing fifth in the championship. His second season with Team LeMans yielded only one point and a seventeenth-place championship finish. He moved to KCMG at the start of 2017, staying for over seven years and claiming four second-place podiums. He did not compete full-time in 2020 and 2021 due to clashing WEC commitments, with Yuichi Nakayama substituting in 2020 and Kazuto Kotaka in 2021. He clinched a podium with third place at Fuji Speedway in 2024 before leaving KCMG after eight seasons. In Super GT, Kobayashi made a one-off debut with Racing Project Bandoh in 2017 and raced full-time with SARD from 2018.
Kobayashi was named after Kamuy, a divine being in Ainu mythology, with the name imitating three Kanji from the sentence "Enabling great dream(s)." In April 2013, he received the Outstanding Achievement in Sport Award at The Asian Awards in London.
Kobayashi returned to the wheel of a Formula One car in June 2025 for the first time in eleven years, driving the Haas VF-23 for the Haas F1 Team at Circuit Paul Ricard, facilitated by Toyota Gazoo Racing's close ties with the Haas team.
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