Cadillac Dale is an R&B singer and songwriter from Detroit. Dale was on track to earn a #1 Hit as part of the duo “Shawn & Dale” with their 1995 single “Soulful Moaning” independently selling 20,000 copies locally. Until Shawn was convicted of double-murder, which ended up squandering the entire record. Fast forward to 2023 where Jack Harlow’s “Lovin’ On Me” earns the thrown atop the Billboard Hot 100 - sampling Dale’s 1995 record “Whatever”. Thrusting Dale into the spotlight and earning him the international credibility he’s deserved for decades.

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CHAPTERS
1:00 How Kyle & Dale connected - thought Dale was dead
4:00 Just focus on making great music instead of “making it”
5:00 People without a million followers could be making way bigger moves
6:30 it happened the way it was supposed to. Most important thing is creating the art
8:00 grew up with MowTown legends
9:45 beautiful disease
11:00 When did Dale start music
12:50 “I’m a rapper that learned how to sing”
13:30 Singing on vacation - wouldn’t let him leave
14:00 got into hip hop after hearing A Tribe Called Quest
15:45 “the reason I think that I can do anything is because of my mother”
16:30 Soggy Bottom Boys
18:00 I owe everything to my mom
18:30 Soulful Moaning Project
20:00 Shawn was incarcerated as their song blew up
21:40 Jack Harlow sampled “Whatever” for “Lovin On You”
23:00 “music is important to Guys like us”
24:00 I would not sacrifice my children for music
25:00 ex-wife broke all his instruments
25:47 “the ball doesn’t have to keep rolling fast, it just has to keep rolling”
26:00 Recorded 175 songs
27:00 didn’t get paid from the label
28:15 how jack harlow came about
29:00 Rihanna wanted to sample “Soulful Moaning”
29:30 connecting with Jack CONT
31:00 riding around the city with Lovin On Me before it came out
31:45 Sean Momberger found the “Whatever” Sample
33:00 song went viral before it came out
33:45 was the song done when they sent it to Dale?
34:00 Detroit lions game
34:55 Met Jack and he said “Thank You”
35:50 jacks great grand dad died at a Detroit lions game thanksgiving day
36:30 Dale all red suit and hat “black Santa clause”
37:00 Responding to the halftime show criticism
38:00 they don’t love it remix
39:45 ultimate collaborator - Biggest rapper in Poland - OSTR
41:00 Jack Harlow halftime show Kyle response
41:45 Not lovin it - people not believing
43:40 Wife Makes Best Soup In North America
44:50: what’s worse than being booed
45:15 “If you look at the mistakes you’ve made and understand them, you know what not to do”
47:00: what would you say to new artists just coming into the industry?
48:45 Rakim The God MC - don’t sweat the technique
50:00 pick up an instrument
51:40 made a song with a guitar he found in the garbage
53:00 Lovin On Me remix
54:45 “Your life wouldn’t be anything without music”
55:49 “IM ALIVE!”