The argument in favor of Theodore consists of three points. Firstly, Theodore likely has the smallest penis (evidenced by his low self esteem throughout the franchise). This would allow Eleanor to most easily preform fellatio. Secondly, Eleanor is a large girl, she knows how to eat. Her weight suggests that her mouth is a precision machine, which might give her an advantage in oral sex. Thirdly and finally, it could be argued that Theodore has ascended to a higher state based on the expression on his face and his relaxed posture. If this is true, Theodore has a strong case for best head.
Working against Theodore is a strong point. He is clearly fast asleep. This means one of two things: either the head was so stale that he passed out, or the head is so good and he’s falling asleep from post nut bliss (but then she shouldn’t be sucking). This simple reality calls into question the quality of the head that Theodore is getting.
Alvin is certainly reacting much more strongly than his brothers, this perhaps shows a superior experience. Most blowjobs do not lead men to doing the jumpman. Alvin may be a chipmunk, but he’s not a chumpmunk, and this ain’t his first rodeo. He’s been shown to be the coolest in his crew and as such has likely gotten some spectacular head in his time. A man of experience reacting as strongly as he is indicates Brittany’s potentially fantastic dome skills.
The quality of Alvin’s experience hinges on the quality of his relationship. Brittany is shown to be the most popular of the Chipettes and thusly may not feel the need to put in the same amount of effort that Eleanor and Jeanette likely are, lack of enthusiasm could be harming her performance. Throughout the movies and source material, Alvin is a dramatic individual who often overreacts to situations creating comedic relief. It is not just possible, but likely, that his over the top reaction is not because he’s getting his soul sucked out, but because he wants to boost the ego of his girl. While this is a valiant effort, blowjobs aren’t theater, they’re honest to god work.
Lastly is Simon. The nerd, the quiet observer, the self proclaimed “smart one”. His geeky status may mean that this is his first sexual experience, and his equally nerdy girlfriend may be for the first time giving head. In the movies, Jeanette is shown to be the most quiet and conservatively dressed of the Chipettes. This prudish lifestyle could be evidence that she won’t get freaky with it.
So - Which chipmunk getting the best head?