Armageddon, put-out inside 1998, based Affleck since a practical main character having Hollywood facility video. A good Often Browse hadn't yet , appeared in the casting processes and you can, after Affleck's screen-test, manager Michael Bay dismissed him while the “a geek”. He was convinced of the music producer Jerry Bruckheimer that Affleck might be a celebrity, although actor had to slim down, feel tanned, and then have his pearly whites capped before filming first started. The movie, in which he played opposite Bruce Willis because the a bluish-neckband driller tasked because of the NASA having ending an enthusiastic asteroid regarding colliding which have Planet, try a box office profits. ” After inside 1998, Affleck got a supportive part given that an arrogant English actor inside the that point intimate comedy Shakespeare in love, starring his up coming-girlfriend Gwyneth Paltrow. Lael Loewenstein out of Range remarked that Affleck “really does a number of their finest really works, suggesting one to funny is generally his genuine calling,” when you are Janet Maslin of the Ny Minutes found your “very comedy”. Affleck after that seemed due to the fact a tiny-city sheriff regarding supernatural nightmare movie Phantoms. Stephen Holden of your own Nyc Minutes pondered why stars instance Affleck and Peter O'Toole got offered to come in the “junky” film: “Affleck's thudding performance implies he or she is learning his conversation to your first-time, right from cue cards.”

Affleck up coming looked contrary Courtney Love throughout the nothing-viewed ensemble comedy 200 Cigarettes (1999)

Affleck and you will Damon got an in-display screen reunion inside the Kevin Smith's religious satire Dogma (just after having starred in Smith's previous clips, Mallrats and you can Chasing after Amy), and that debuted at 1999 Cannes Film Event. Janet Maslin of your New york Times pointed out that the two, to play fallen angels, “provide higher, understandable warmth to help you Mr. Smith's smart cam and you can wild imaginings”. Affleck starred contrary Sandra Bullock throughout the personal comedy Forces out-of Characteristics (1999), to play a groom whoever attempts to arrive at their matrimony is actually challenging by his free-saturated travel spouse. Owen Gleiberman regarding Activities Weekly remarked that Affleck “gets the prompt-crack appeal you want within the a screwball character,” when you find yourself Joe Leydon out-of Range acknowledged “his profitable capability to play facing their apperance within the a self-effacing comic turn”.

Shakespeare crazy acquired eight Academy Honors, and Finest Visualize, as the cast claimed the Display screen Stars Guild Honor getting A fantastic Abilities of the a tossed

Shopping for a directorial profession, Affleck shadowed John Frankenheimer during the pre-creation of the experience thriller Reindeer Online game (2000). Frankenheimer, leading their past ability film, discussed Affleck as the having “an extremely effective, likable high quality in the him. I have been doing so for quite some time and you may he is really among the many best.” The guy starred opposite Charlize Theron as the a great hardened criminal, with Elvis Mitchell of Ny Moments experiencing the unexpected casting selection: “Affleck usually ways among the many Kennedys to experience Clark Kent ... He appear as if he's got never ever missed a party or good night of bed. He or she is video game, although, and his slight dislocation works to the main benefit of Reindeer Online game.” He then had a supporting role because an excellent high pressure stockbroker within the the fresh new offense drama Boiler Area (2000). Good.O. Scott of your New york Times felt Affleck got “traced more than” Alec Baldwin's results inside the Glengarry Glen Ross, if you're Peter Rainer of the latest York Journal said the guy “does a series of riffs on the Baldwin's aria, and every one is funnier and you will crueler as compared to next”. Then he provided the voice out of Jos. Inside the history flick part of 2000, Affleck played contrary their partner Paltrow about romantic drama Jump. Stephen Holden of your Nyc Minutes praised the fresh “understated strength and you will superb detail” from their performance: “His portrait off an earlier, sarcastically thinking-outlined ‘anyone person' spotted who's not half of as convinced when he want to appear is virtually decisive.”