マツコがこんなグイグイなの初めて見たかも。やっぱり千葉さんのカリスマ性って底しれねぇ。

English Translation

This might be the first time I’ve seen Matsuko being this aggressive/pushy. Chiba’s charisma is boundless.

Let me break down these two sentences in detail, looking at their grammatical components and nuances:
First sentence: マツコがこんなグイグイなの初めて見たかも。
(Matsuko ga konna guigui nano hajimete mita kamo.)
マツコが (Matsuko ga)

マツコ: Proper noun referring to Matsuko Deluxe
が (ga): Subject marker particle, emphasizing Matsuko as the topic being discussed

こんな (konna)

Demonstrative adjective meaning “this kind of” or “like this”
Used to point to a current or just-witnessed situation

グイグイ (guigui)

Mimetic/onomatopoeic word describing forceful or aggressive forward movement
Often used to describe someone being pushy or forward in their behavior
Doubled for emphasis, which is common in Japanese mimetic words

なの (nano)

な (na): Conjugating particle used after na-adjectives
の (no): Nominalizing particle that turns the preceding phrase into a noun
Together they turn グイグイ into a nominal phrase

初めて (hajimete)

Adverb meaning “for the first time”

見た (mita)

見る (miru): Verb meaning “to see”
た (ta): Past tense marker

かも (kamo)

Contracted casual form of かもしれない (kamoshirenai)
Expresses uncertainty or possibility (“maybe” or “perhaps”)

Second sentence: やっぱり千葉さんのカリスマ性って底しれねぇ。
(Yappari Chiba-san no karisuma-sei tte soko shirenē.)
やっぱり (yappari)

Adverb meaning “as expected” or “after all”
Shows that something confirms the speaker’s expectations

千葉さんの (Chiba-san no)

千葉 (Chiba): Proper noun (person’s name)
さん (san): Honorific title
の (no): Possessive particle

カリスマ性 (karisuma-sei)

カリスマ (karisuma): “charisma”
性 (sei): Suffix meaning “-ness” or “quality of”
Together they mean “charismatic nature”

って (tte)

Casual topic marker, equivalent to formal という or は
Often used in spoken Japanese

底しれねぇ (soko shirenē)

底 (soko): “bottom” or “depth”
しれない (shirenai): “cannot know” or “unknowable”
ねぇ (nē): Very casual pronunciation of ない (nai)
Together they form an idiom meaning “unfathomable” or “bottomless”

The complete translation would be approximately:
“This might be the first time I’ve seen Matsuko being so forward/pushy. As expected, Chiba-san’s charismatic appeal is truly boundless.”
The overall tone is quite casual, as shown by:

The use of かも instead of かもしれない
The colloquial って instead of は
The very informal ねぇ instead of ない
The use of やっぱり instead of more formal やはり

This appears to be a comment about observing an interaction between Matsuko and someone named Chiba, expressing surprise at Matsuko’s unusually forward behavior while acknowledging Chiba’s impressive charismatic influence.