Q 01/05

The T in T-Pain's stage name stands for which city, where the singer was born and raised?

A) Tuscaloosa

B) Thomasville

C) Tallahassee

D) Texarkana

Answer · why

C) Tallahassee

Tallahassee Pain was the full name, chosen for the hardships he went through while living there.

Q 02/05

T-Pain won the first season of The Masked Singer in 2019 while disguised as which character?

A) Monster

B) Peacock

C) Rabbit

D) Unicorn

Answer · why

A) Monster

Monster beat Donny Osmond's Peacock into second place and Gladys Knight's Bee into third.

Q 03/05

Which rapper's debut single 'Low', featuring T-Pain, spent ten straight weeks at number one in 2008?

A) Soulja Boy

B) Sean Kingston

C) Lil Jon

D) Flo Rida

Answer · why

D) Flo Rida

Flo Rida's hit was the most downloaded single of the 2000s and was later certified Diamond.

Q 04/05

Which singer joined T-Pain for 'Thug Story', a parody of her own hit, at the 2009 CMT Music Awards?

A) Carrie Underwood

B) Taylor Swift

C) Miranda Lambert

D) Kelly Clarkson

Answer · why

B) Taylor Swift

Taylor Swift and T-Pain rapped and sang through Auto-Tune in the spoof of 'Love Story', which aired as the ceremony's cold open.

Q 05/05

T-Pain earned a Grammy nod for 'I'm on a Boat', a Saturday Night Live short by which comedy group?

A) The Lonely Island

B) Tenacious D

C) Garfunkel and Oates

D) Human Giant

Answer · why

A) The Lonely Island

The Lonely Island wrote the whole song and sent it over; T-Pain, confused by the premise at first, added his voice and sent it back.