Since the conception of social media, research on political communication has pointed toward the risk that the social media environment can foster political echo chambers. However, this has recently been contradicted by some studies demonstrating “cross-cutting discussions” on social media. The current study extends this literature by particularly focusing on communication on political vlogger videos and having mainstream news outlet videos as a reference point. Specifically, this study addresses five points: (1) to what extent cross-partisan comments occupy conservative and liberal vloggers’ comment threads and if there is a significant difference between the two, (2) the possibility that comments from vlogger videos can be utilized to predict the political leanings of comments on mainstream news outlet videos, (3) if the proportion of cross-cutting discussions on mainstream news outlet videos significantly varies by the news outlet’s political leaning, (4) if a neutral news outlet channel can work as a venue for cross-cutting discussions, and (5) if the proportion of cross-cutting comments in mainstream news outlet comment threads is significantly different from that in vlogger comment threads. Both manual and computational analyses were employed; the political leanings of vlogger comments were analyzed by manual content analysis, and based on the results, the political leanings of mainstream news outlet comments were analyzed by NLP classifiers using three different algorithms—logistic regression, SVM, and random forest. As a result, we found that the proportion of cross-cutting discussions significantly varies by both the channel’s political leaning and media type. In addition, our results suggest the possibility of neutral news outlets as a place for cross-cutting discussions.