The Jewish neocon anti-Islamists are cringe because they are a holdover from a time a bit before any pretense at anyone on the right being edgy or subversive. They love Bush, war, Raytheon, and believe the borders of Israel are more important than the borders of the US, Europe, or any other western nation or entity. They've discovered an edgier right exists, but attempts to imitate it come off like a boomer parent trying to reach their millenial children by adopting some of their mannerisms, not realizing that these children have shifted drastically on their views of Islam. They may still not want it in their country, but rather than seeing a fellow western ally in Israel, they look at the conflict and see parallels between the Palestinians losing their homeland and losing their own countries to whatever immigrant group is invading at the moment, something Shapiro and his ilk have said they are perfectly fine with as long as Israel stays Jewish.
I actually have some use for Lauren Southern, a lot more than Ben Shapiro at least. Shapiro's anti-Islamism seems to come only from a desire to protect Israel, while Southern seems to have a semi-coherent anti-immigration ideology. She no doubt has some of her own cringe and drama that follows her though. I still think her "Allah Us" and "Allah is Gay" was a decent troll though.