Affleck then searched reverse Courtney Like throughout the nothing-seen ensemble comedy 2 hundred Tobacco (1999)
Affleck and you can Damon got an in-display reunion for the Kevin Smith’s spiritual satire Dogma (after having starred in Smith’s past video, Mallrats and you will Chasing after Amy), and that debuted during the 1999 Cannes Motion picture Event. Janet Maslin of the Ny Minutes remarked that the pair, playing dropped angels, “offer higher, understandable enthusiasm to Mr. Smith’s wise cam and insane imaginings”. Affleck starred reverse Sandra Bullock regarding personal comedy Forces from Nature (1999), to relax and play a bridegroom whoever tries to get to their matrimony are difficult by their free-competing traveling mate. Owen Gleiberman out of Enjoyment A week pointed out that Affleck “has got the fast-crack charm you prefer for the an effective screwball character,” if you are Joe Leydon regarding Assortment applauded “their profitable capacity to enjoy up against their good looks during the a beneficial self-effacing comical change”.
Shakespeare in love acquired seven Academy Prizes, and Greatest Visualize, since cast obtained the fresh new Screen Stars Guild Prize for A great Results because of the a thrown
Searching for an effective directorial occupation, Affleck shadowed John Frankenheimer during pre-creation of the experience thriller Reindeer Video game (2000). Frankenheimer, pointing their last function motion picture, explained Affleck due to the fact with “a highly profitable, likable high quality about your. I’ve been this for a long period and they are extremely one of several nicest.” He starred reverse Charlize Theron since a great hardened violent, which have Elvis Mitchell of Nyc Moments experiencing the unanticipated casting alternatives: “Affleck commonly means one of the Kennedys to relax and play Clark Kent … He appear as if he’s never skipped a celebration otherwise good night’s sleep. He or she is online game, regardless if, and his moderate dislocation actively works to the advantage of Reindeer Game.” Then got a supporting character since the a great high-pressure stockbroker inside brand new crime drama Boiler Room (2000). A.O. Scott of the New york Minutes thought Affleck had “traced over” Alec Baldwin’s abilities in the Glengarry Glen Ross, when you are Peter Rainer of brand new York Journal said the guy “really does a number of riffs on the Baldwin’s aria, and every you’re funnier and you can crueler compared to the 2nd”. Then given brand new sound out of Jos. In the past flick character of 2000, Affleck played reverse his spouse Paltrow on personal crisis Bounce. Stephen Holden of the Ny Times acknowledged the new “simple strength and you may exquisite detail” regarding his abilities: “His portrait out-of an early, sarcastically worry about-laid out ‘anybody person‘ who is not 1 / 2 of as convinced when he want to seem is practically definitive.”