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The relationship between Rochester and Benny became more complex and familiar as the popularity of Rochester's character grew, with Rochester's role becoming both less stereotypical (in early episodes he carried a switchblade) and less subservient (though he remained a butler). As a butler he was subservient to the entire cast and was addressed as Rochester, but addressed the other characters as Mr. and Miss. Although Dennis Day's character is much younger and an idiot, Rochester respectfully addressed him as Mr. Day. Rochester often outwitted Benny, by getting Benny to mop the floor, for example.<ref name="Boskin, pp. 175-187"/><ref name="Smith, p. 17">Smith, p. 17.</ref>
The "Rochester" character retained many of the stereotypes (lazy, gambler, drinker), but they became a part of his character, disassociated from his race{{according to whom|date=February 2022}}. Even though some of the humor was stereotypical, it was always done so that the racial element of the joke came from Anderson and no one else.<ref name="Gates, p. 7"/> In a February 1940 multi-episode radio play in which the gang visits [[Yosemite National Park]], Rochester bemoans about having to constantly sing songs for Jack (in order to make up for the lack of a radio in their car). Worse still, he says, "at eight o'clock he wants me to imitate 'Amos and Andy'". After a pause for audience laughter, he continues: "I can't do that blackface stuff!" Later, Rochester asks Benny if he can walk around and explore at [[Badger Pass Ski Area|Badger Pass]]. Jack consents, but warns Rochester not to "get lost in the snow", to which Rochester replies, "Who me?"
During [[World War II]], Benny toured with his show, but Rochester did not, because discrimination in the armed forces would have required separate living quarters. However, during performances of the radio program staged before armed forces audiences at bases and military hospitals, the appearance of Rochester routinely drew enthusiastic applause that arguably often outstripped that received by other members of the cast, more so than in civilian audiences.{{citation needed|date=January 2017}} Also referenced in Benny's posthumous autobiography, ''Sunday Nights at Seven'', was an episode at the conclusion of a broadcast originating at a military base which featured Rochester. Benny was reportedly at a table mingling with soldiers, when one serviceman told Benny how he thought Rochester was really funny and one of his favorites. Benny asked if he would like to meet him, but the soldier declined saying that where he comes from whites don't sit with people like Rochester. Appalled, Benny reportedly told him off and left the table.
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On the 1968 special ''Jack Benny's Bag'', Benny introduced Anderson as "my lifelong friend, Rochester" and asked Anderson to work with him on a new television series. The plots brought up by Benny were of recent or current television shows, with Anderson reminding him that this had already been done. Benny then asked Anderson about coming back to work for him as his valet. Anderson replied, "Hold it, Blue Eyes, we don't do that any more."<ref name=Reunion/> The following year, Rochester appeared again in the special ''Jack Benny's New Look'', where Rochester drives Benny home in a [[Rolls-Royce]] after Benny's meeting with Gregory Peck to discuss appearing as a guest star.
'''Benny''': "Well Rochester, congratulate me. Gregory Peck said that he would be on my show."
'''Rochester''': "Good, good. I'll bet you had to pay him a lot of money."
'''Benny''': "You're wrong. He's going to do the show for nothing
'''Rochester''': "How did you do that?"
'''Benny''': "Because I'm a very good salesman. I didn't come right out and ask him. I was very subtle."
'''Rochester''': "What did you do? Did you cut your wrist?"
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